Stunning Water Views from ''Windward'' on the Bay

Another Outstanding Stay at Windward

This is our third consecutive year renting Windward for our extended family. Elisabeth and Doug are extremely thoughtful hosts, ensuring that their guests have everything they need in a beautifully maintained house to have an exceptional vacation. The house is well equipped, so much so that you truly only need to bring your clothes! All the beds are very comfortable, the kitchen extremely well equipped and there is plenty of room for 8 adults to spread out. The location is peaceful with gorgeous sunset views and convenient to everything on the outer Cape. We will definitely be back for year 4!

Stayed: August 2024 Submitted: October 24, 2024

Glorious Stay

This is our third consecutive year renting Windward for our extended family. Elisabeth and Doug are extremely thoughtful hosts, ensuring that their guests have everything they need in a beautifully maintained house to have an exceptional vacation. The house is well equipped, so much so that you truly only need to bring your clothes! All the beds are very comfortable, the kitchen extremely well equipped and there is plenty of room for 8 adults to spread out. The location is peaceful with gorgeous sunset views and convenient to everything on the outer Cape. We will definitely be back for year 4!

Stayed: August 2024 Submitted: October 22, 2024

Spectacular family vacation at Windward!

I had trouble finding just the right spot for my husband’s 75th birthday celebration where we could accommodate his four grown children and his three year old granddaughter as well as ourselves. Windward had all the answers! It has the perfect location with a gorgeous view and quiet surroundings. The kitchen is fully loaded with every spice and utensil you could need. Before you go grocery shopping make sure you check this kitchen out so you won’t buy something that’s already there! From the beach chairs and toys to the explicit directions about whatever you might need, Douglas and Elizabeth provide everything down to the last detail. It is so homey there. It does not have the coldness that some other rental properties do. it is close to ocean beaches, bay beaches and pond beaches. Be sure to check them all out as the sticker you need for your car will allow you to park at any and all of these spots. The outdoor showers are fantastic after a day at the beach. The gorgeous deck is the perfect place to unwind after a long day and watch the beautiful sunset. There is a fantastic grill out on the deck that we didn’t use in this circumstance, but I would if I went back again. The landlords are very attentive to your every need and will come and help you in person if need be. It was perfect for everyone from the three year-old to the 75-year-old! If you’re looking for an authentic Cape Cod experience, look no further than Windward!

Stayed: August 2024 Submitted: September 12, 2024

Wonderful home rental

This was our first stay at Windward, with 8 people. The home is very clean, comfortable and well-appointed, and the view is fabulous. There is access to the bay beach via Indian Nauset Trail nearby, it was very nice for walking. It was also easy enough to drive a short distance to launch our kayaks. The neighborhood is quiet. The location is also very convenient to popular spots in Wellfleet. Douglas and Elisabeth provided all the beach items needed, which truly saved space when packing the cars. They also provided shower items, sunscreen and bug spray for each person. The kitchen is updated and spacious. The outdoor shower is large and private. We will definitely consider staying at Windward again next time we visit Cape Cod.

Stayed: August 2024 Submitted: September 05, 2024

We loved Windward!

We spent two glorious weeks at Windward with our family - 4 adults, 2 teens, and 2 dogs. It was perfect for our group - very unique house with a high level of craftmanship - very clean and lots of of amenities. The upstairs living area has a gourmet kitchen and big windows that provide amazing views of the marsh, tides, and sunsets. The outdoor shower is fabulous - the best we have encountered on the cape. A good location on a quiet road - with easy access to walking trails, including along Blackfish Creek. We enjoyed meeting the incredibly nice and responsive owners. We would definitely consider returning to this beautiful and charming house.

Stayed: July 2024 Submitted: August 11, 2024

Another perfect vacation at Windward!

Our family recently returned from another perfect 2 week stay at Windward. The house, like last year, is immaculate and incredibly well-appointed. Douglas and Elisabeth are wonderfully attentive hosts and made sure we had everything we needed, and more. It is clear they put a lot of thought and care into providing a comfortable and luxurious stay for their guests. HIghlights of this beautiful cottage nestled in Wellfleet were breathtaking views of the marsh at sunrise and sunset, taken in from the expansive deck, and kayaking in the marsh. Note - Jack's boat rentals delivers boats right down to the marsh for Windward guests. We have already booked our stay at Windward for summer 2025 and cannot wait to be back!

Stayed: July 2024 Submitted: July 30, 2024

Spectacular views and comfort galore!

I just spent a very relaxing week at Windward. The home is equipped with everything one could possibly need with all the comforts of home. My family loved the deck and the wonderful ever-changing views of Blackfish Creek. I spent a lot of time in the reading nook with a beautiful view of the water. Even if someone was watching tv, the nook was quiet, comfortable, and peaceful. The home has space for everyone with a thoughtful layout. This is the perfect home for a family to spend time together as well as relax in your own space. The beds are amazingly comfortable too! The quiet surroundings and a walk along Nauset Trail adds to the charm of this splendid location.

Stayed: June 2024 Submitted: July 06, 2024

Another Amazing vacation stay at Windward!

Having stayed at Windward in May of 2021, my family and I were so delightfully surprised that Windward was available for this spring as well. It was wonderful to spend 4 weeks, with my family, including my husband, 2 sons, and 2 daughters. While I was expecting Windward to be special; having spend a couple of weeks in 2021 also, I had no idea how much more special I was these 4 weeks in 2024.The Ingrams provided caddies for each individual vacationer to use for the outdoor shower, which was amazing! The Ingrams supplied much more to use in kitchen; for example, Dunkin Donuts coffee pods for kuerig, coffee beans/ ground coffee for drip coffee maker, teapot with umpteenth amount of types of teas. The amount of spices, sugar, flour, bisquick, utensils, ect, definitely came in handy for easy cooking. My children loved pancakes and maple syrup (provided at Windward) for me to make a great “d fashioned “ breakfast.The amount of linens, toiletries, extra sheets, toilet paper, paper towels, napkins, medicine available to access in bathroom cabinets, for which all we needed, and very thankful items were available to us.Windward was extremely clean and organized, which felt very welcoming to us right away. We really appreciated all of the live indoor plants, from in each bedroom, to the dining area. Lots of plants and beautiful bushes outside for us to enjoy as well. We also enjoyed on sunny days overlooking the water, low and high tide, and gorgeous sunsets, either viewed from the dining/ living room area, to relaxing on the top deck. Sure was breathtaking at times.My family and I highly recommend Windward in all areas as five stars in every aspect of our vacation. We will definitely put in place with our plan to return either spring or fall 2025, for which we prefer coming on either side of summer, traffic is a bit less, yet many , most restaurants and amenities are available as well.

Stayed: May 2024 Submitted: June 21, 2024

Outstanding Cottage and View

Our family returned to this cottage a second season because of the unsurpassed view and peaceful surroundings. The upstairs contains a fully-equipped kitchen with modern appliances. Since the cottage is minutes from Hatch's fish market, we chose to cook fresh seafood every evening. We enjoyed sitting on the upstairs deck every morning with our coffee and to view the wonderful sunsets. The king sized beds on the lower level are so comfortable we all slept comfortably from the first night. The location also makes it easy to bicycle from the cottage to the rail trail, the Old Wharf and ocean view drive.

Stayed: June 2024 Submitted: June 21, 2024

Breathtaking water views and sunsets!

We spent a wonderful week at Windward. The water views and sunsets were incredible. The post and beam style upside down house was beautiful. There were fresh cut flowers in all the bedrooms. The potted plants that didn’t need watering added to the ambience of the home. The house was sparkling clean.The kitchen had everything you could possibly need. Windward is close to bay, ocean, and pond beaches. Also close to restaurants, grocery stores, galleries, shops, boutiques, rail trail and Audubon Sanctuary. We spent a relaxing week in a beautiful home!

Stayed: September 2023 Submitted: November 11, 2023

Wonderful Family Vacation

The Windward was an amazingly beautiful home. The woodworking and all of the added custom details was just beyond anything we had imagined. The view from the cottage is incredible and we spent time watching the gorgeous sunsets each evening. There was plenty to do and everything was a short drive. The home was beautifully appointed and had absolutely everything that anyone could need. This was a fantastic place to take a vacation. Can’t wait to return!

Stayed: September 2023 Submitted: October 31, 2023

Another Outstanding Stay at Windward

After spending one week at Windward in 2022, we decided it wasn't enough and booked two weeks in 2023 and thrilled again with our experience. The property is lovingly cared for by the owners and every amenity is taken care of. The kitchen is wonderfully stocked with essentials, there are plenty of towels and beach towels and all the beach items you could possibly need. I particularly like the comfort of Windward...there is plenty of space for everyone to spread out and not be on top of each other and many cozy options for curling up to read a good book, watch the gorgeous sunsets, the ever changing tidal marsh views or tune out to TV. I also appreciate the modern bathrooms and the TWO outdoor shower spaces. The location is perfect...very quiet and peaceful but a short ride to restaurants, ocean and bay beaches and the Wellfleet Kettle Ponds. We even brought our bikes this year and easily biked to the Cape Cod Rail Trail. Elisabeth and Douglas are super conscientious h

Stayed: August 2023 Submitted: October 27, 2023

Excellent rental

Certain homes have a pleasant aura about them, we found Windward to be one of them. Four of us rented Windward in September and enjoyed an excellent week. The location was perfect for enjoying the outer cape, close to many beaches on the bay and ocean side, very good restaurants and attractions nearby. Windward was very clean upon arrival and loaded with a fully equipped kitchen. we enjoyed many meals on the upper deck, overlooking a spectacular view . The house also had all of the necessary amenities needed to make an enjoyable vacation. The hosts were very accommodating . we will return to windward.

Stayed: September 2023 Submitted: September 26, 2023

Heaven on earth

The owners of Windward went above and beyond to ensure we had an unforgettable two week vacation. First, the setting on the water is spectacular with views for days! The location is fantastic- close to beaches and a quick drive to town. The house is completely stocked with anything and everything you would need. The kitchen has anything a gourmet chef would need, including dozens of spices. We were also provided with coffee pods for the Keurig and new coffee for the regular coffeemaker! The bedrooms all had clean sheets and towels, plus fully stocked bathroom caddies for each person that included new shampoo, soap, bug spray, sunscreen, and many other items. The home is also stocked with everything you need for the beach including beach towels, blankets, chairs, umbrellas, coolers, etc. The owners are readily available for any questions or concerns and could not be nicer. The house had vases of fresh cut flowers upon our arrival in every room! The decor is cozy and comfortable, with beautifully updated bathrooms and kitchen. The outdoor spaces are also great, and there are very handy outdoor lines to hang towels after a day at the beach. We loved the large, newer outdoor shower as well. The owners have thought of everything and we cannot wait to return!

Stayed: August 2023 Submitted: September 05, 2023

Idyllic Escape

My family recently had the privilege of staying at this lovely vacation rental, and it truly exceeded all expectations. From the moment we arrived, we were greeted by the most breathtaking sunsets which we enjoyed every afternoon from the well furnished deck.The rental itself was a haven of comfort and convenience. It was abundantly clear that Elisabeth and Douglas had put a lot of thought and care into making sure every guest's needs were met. The place was incredibly well-stocked – from the kitchen essentials to the bathroom toiletries to a great selection of books, we lacked for absolutely nothing. This attention to detail made our stay so much more enjoyable, as we didn't have to worry about running out for basic supplies.What truly sets this vacation rental apart is its prime location right on the bay. The proximity to the bike trail was another highlight – we spent our days exploring the area on two wheels, surrounded by nature's beauty. Our daughter/son-in-law were even able to commute there from the Provincetown ferry on their bikes! Marconi beach was only a 5 minute ride away and is truly one of the most beautiful beaches on the Cape.In conclusion, our stay at Windward was wonderful. The stunning sunsets, the well-thought-out amenities, the bay-side location, and the evident passion that went into its creation made it a true gem. If you're looking for a place to unwind, reconnect with nature, and bask in the comfort of a home away from home, Windward should be your top choice.

Stayed: August 2023 Submitted: August 29, 2023

Magical stay in South Welfleet!

This was truly the most magical vacation home we have ever stayed in. The views alone are enough to recommend this home, but there is much, much more. The house is fully stocked with absolutely everything you could ever want or need - from cooking supplies to towels, extra blankets, plenty of beach reads, and even a personal caddy for every guest that includes all the things you might forget, like sunscreen, shampoo, aloe, and razors. The decor is casual and elegant with plenty of seating for a spectacular view of the marsh - whether from inside on a cloudy day or sitting on the deck, or on the hammock in the ample front yard. The Ingrams have thought of everything to make guests feel welcomed and cared for. We have already booked our stay for next summer and cannot wait to return.

Stayed: July 2023 Submitted: August 07, 2023

Windward Forever!

We had a magnificent week at Windward. The property and setting were even better than the photos and the owners could not have been better hosts. My parents -- ages 86 and 91- enjoyed the master bed and bath and spent days out of the sun on the lower patio enjoying spectacular views of Pleasant Point and Great Island. the rest of us enjoyed lounging on the 2nd floor enjoying the cozy spaces, fabulous kitchen and spectacular views. Windward is a real home -- and becomes that for the people who stay there. We will treasure our memories from this week -- and are so grateful to Elisabeth and David for taking care of us and their lovely Wellfleet retreat.

Stayed: July 2023 Submitted: August 03, 2023

Windward Wonder

On a quiet walk in Spring of 2022,we came upon Windward cottage. We experienced awe and admiration of the architecture and view of the marsh. We found this home listing and immediately contacted the owner to reserve for Sprng 2023. Our wonder expanded when we first entered the cottage on June 3, 2023. The views of the marsh from the living areas and master bedroom are unsurpassed. Our family of six decided to prepare dinner in the fully-equipped, well-appointed kitchen every evening. When it was my turn to prepare dinner, I would turn on classical music and dreamily take my time in the moment, while looking at the view. Hatch's Fish and Produce is nearby in the village of Wellfleet. Most of their seafood is fresh daily, as well as oysters from their own beds. A rainbow appeared over the marsh our first morning. Days were spent bicycling and hiking the known and less known trails around Wellfleet, as well as gazing at the ocean from the town beaches. The ponds are nearby and offer swimming. We brought a kayak, which can be launched in some ponds and the marsh below the cottage. Evenings were spent reading or working puzzles, listening to the wind and sometimes the rain. We slept well in the comfortable beds. We all appreciated the on-suite bathroom and shower, extra nearby bathroom with tub and shower, upstairs toilet near the living area, and outdoor shower. Linens and towels are provided, as well as a washer and dryer. There are plenty of restaurants, shops and art galleries nearby, as well as theatre, and the Wellfleet Drive-in. Our daughter and her fiance biked from the cottage to the Provincelands and back in four hours. We discover something new every year, and Windward is a joy to return to each day.

Stayed: June 2023 Submitted: June 19, 2023

Picture perfect!

What a vacation this was! Douglas and Elisabeth gave us extensive information on the house and town before we even arrived. Upon our arrival, Elisabeth greeted us warmly, had a few thoughtful "welcome to our home" gifts, gave us full tour of the house, and even strolled the neighborhood with us to show us where the trails to the water were. They checked in to be sure we were happy with everything.The house is even better than the photos show. There are so many nice little decorating touches that you just can't capture in a photograph. It is all sea themed and often Wellfleet themed, with paintings and sculptures by local artists. It manages to be roomy and cozy at the same time. The post and beam construction surrounds you with beautiful wood . The kitchen is incredibly well stocked. The custom designed cabinets make excellent use of space, the appliances are new, and whatever you need is there and organized meticulously. The bedrooms are charming, the beds were very comfortable, Linens and towels are supplied. There was ample seating in both the dining room and living room, and no less than four outside sitting areas. The views of the water and the sunsets are spectacular. If you don't like sand, just sit on the deck, enjoy the sun, and be surrounded by water views. The neighborhood was quiet and delightful to stroll and bike. The woodworking in the master bath is simply beautiful and all the bathrooms look like they have just been remodeled. Even the fixtures are elegant. It could be the cleanest house we have ever stayed in.May can be a bit unpredictable, but we were blessed with a spectacular week of sunny weather in the 60's and 70's. There are lovely trails (in Wellfleet at Marconi, in the Province Lands, and the Audubon Sanctuary), numerous kayaking sites, a wonderful gym called Heart Core, Catholic Masses are available in Wellfleet, P-town and Orleans, lovely bay and Ocean beaches, and of course the Cape Cod Rail Trail. We were able to find gluten free fare at Montano's, Three Fools, the Rail, Far Land Provisions and PB Boulangerie. Wellfleet Marketplace is great store that has just about everything and is oozing with local flavor!This vacation was picture perfect.

Stayed: May 2023 Submitted: May 20, 2023

Lovely Windward

Windward was everything we expected and more. Very clean and meticulously taken care of. Great communication with owners. Close to incredible beaches and restaurants. Would love to come back!

Stayed: September 2022 Submitted: December 30, 2022

A month of quiet and beauty

My husband and I decided to try staying a month at one of our favorite places, Wellfleet, and were so lucky to find Windward. The beautiful, ever changing bay and marsh became our best friend. We enjoyed a wide range of weather including many beautiful fall days. The house is very well equipped and has great character. Now back at home, I miss being there!

Stayed: October 2022 Submitted: November 04, 2022

Stellar Views, Great House

If you live for amazing Cape views this is the house for you. With views on both levels, the experience staying for a week was just an amazing delight. For those concerned with other essential things like comfortable beds and a well-stocked kitchen., you have also found the right place. Top of the line appliances and a fully stocked kitchen are prime features of this kitchen. There is also a really nice deck that overlooks the Bay. Finally, the house is very well stocked with beach equipment -- umbrellas, chairs and much much more

Stayed: August 2022 Submitted: September 22, 2022

Great House, Great Views

Watching the ever changing landscape of the tidal marsh, gorgeous sunset cocktail hour on the deck, plenty of comfy couches for lounging and reading and every detail thought of sums up our week. Elisabeth and Doug have created a beautiful oasis and are super conscientious in ensuring you have the best, more carefree vacation at their house. This is the 7th house I've rented on the Cape over the last 20 years and definitely the best. Honestly the photos don't capture the specialness of this home.

Stayed: August 2022 Submitted: September 11, 2022

Lovely Wellfleet home

Our family recently spent at week at Windward and thoroughly enjoyed the house and the location. We were a group of 8 adults, 4 couples, and one very happy Bichon Frise. The house is a wonderful work of art and was immaculately clean and well cared for. The owners were very attentive and responsive, both in advance of the vacation as well as during our stay whenever a need arose. We we all charmed by the location, the peace and quiet, and the spectacular view from the deck, the grounds, and many rooms in the house. The sunsets are definitely amongst the best we've ever seen in Wellfleet.

Stayed: August 2022 Submitted: September 04, 2022

Perfect retreat

From the location overlooking an inlet to Cape Cod Bay, the property and surrounding areas are a perfect setting. The house is clean and comfortable. Elisabeth and Douglas provide all the amenities for staying at the house or going to the beach. The house is located within a short driving distance to 20 different beaches, the town and many restaurants. They were very helpful in making recommendations for beaches, restaurants or sites of interest. I've already discussed with them coming back next year. I would not hesitate to recommend this property.

Stayed: July 2022 Submitted: July 27, 2022

AMAZING

My wife and I stayed at Windward for seven nights at the beginning of July. In one word, our experience was "exceptional." Elisabeth and Doug were wonderful, attentive, hosts who provided is with all the information about Windward that made the week fly by. So the sunsets from the deck are amazingly beautiful; the changes in the bay waters are a wonder to behold; the accoutrements in the house are very tastefully and aesthetically pleasing; very user-friendly kitchen, SPOTLESS house, quiet, and serene. Close to restaurants and five minute drive to center Wellfleet. We highly recommend staying ate Windward. What a find!

Stayed: July 2022 Submitted: July 12, 2022

Amazing Wellfleet Sunsets

Awesome sunsets in WellfleetGuest Review: My husband and myself along with our 4 adult children had the pleasure of renting Windward the last week in June. We have traveled and rented homes often and this was by far the most organized and well stocked home we ever rented. From bedding to beach toys to a state of the art stocked kitchen they had it all! There is nothing you needed to bring. My two Favorite parts were how everything in the house was labeled and how each room had shower caddies for each person filled with toiletries, sunscreen, after sun lotion, razors, and so much more.Of course the icing on the cake was the most beautiful views overlooking the water along with breathtaking sunsets.Elisabeth and Douglas supplied us with so much literature regarding restaurants, beaches , ice cream places, cape cod history and more. They were easy to communicate with before and during our week visit and were available to help us the when asked. They even held on to our daughters bathing suit that we left behind so we could get it back!Thank you for opening your beautiful home to renters and we look forward to renting again.

Stayed: June 2022 Submitted: July 09, 2022

Windward

I can’t think of a better place to spend a week on Cape Cod than at Windward. Located on a tidal marsh off of a quiet dirt road, the setting felt remote and yet was only minutes to beaches,trails, restaurants and galleries. The house itself was charming, warm, and rustic - beautifully designed and maintained. The furniture was lovely, and the kitchen was equipped with everything you can think of. The deck, which overlooks the marsh, (as do most of the rooms in the house) was the perfect place to eat a meal, watch the sunset and just relax.   Elisabeth sent us lots of information about Wellfleet even before we arrived, and clearly attends to every detail to ensure a wonderful vacation. We would definitely stay here again.

Stayed: May 2022 Submitted: July 07, 2022

Little Piece of Heaven

I booked Windward in early January. Having family from the Cape, we felt it was time to get back “home” even if only for a week. I came upon Windward as I’ve used this booking site in the past and have never been disappointed. I’ll list the pros and the cons.Pros: location is excellent for those who like to be closer to PTown, Nat’l Seashore, and a bit less craziness the Cape can have! The house is very well stocked with kitchen requirements, extremely comfortable, organized (something I appreciate!), and the sunsets are glorious! The house matches the pictures on the website; quincentennial cape cod appeal. We loved the house.Cons: We went in early June when ticks are just waking up looking for hosts. Thanks goodness our small non-shedding dog is white! I am used to doing tick checks living in a mountainous area, but the ticks were pretty bad. Spraying the grassy area around the house would help, but may not be allowed for conservation purposes. We all did tick checks and managed it.Too much contact prior to arrival, and during stay with owners. I appreciate the owners being selective with whom they rent to. I spoke with the owner, Elisabeth, for over an hour when interested in booking Windward, we were sent a 17 page instruction booklet, asked to have a half hour conversation day before we arrived, along with being asked for an hour in person orientation upon arrival. Too much and not necessary. It felt like a lot of “work” just to begin our vacation. This regiment might be something to consider changing. It felt a tad intrusive.All in all, we had a lovely time. The owners of Windward love their home, and it shows.

Stayed: June 2022 Submitted: July 05, 2022

Oasis on the Water

Windward is a wonderfully clean and perfectly quirky home located central to delicious restaurants, national seashores and all kinds of outdoor activities (hiking, biking, mini golf, etc.). The hosts stock the house with everything you could imagine, making packing a breeze. The home is big enough to provide privacy for anyone looking for it and quaint enough to get in some great family time. I highly recommend Windward!

Stayed: June 2022 Submitted: July 05, 2022

Beautiful home - lovely views - very comfortable

Windward is a lovely home with the most beautiful views. The kitchen has everything you will need and you can watch the gorgeous sunsets from the deck or from the living room and dining room. Owners are very responsive and respectful of guests' privacy. Location is lovely - beautiful walk on dirt roads to the bay; close to the best French bakery on the Cape; very close to Marconi Beach and an easy ride into Wellfleet or Provincetown.

Stayed: May 2022 Submitted: June 28, 2022

Wow!

Wow! This rental has it all! Beautiful, COZY home…all the amenities you could ask for…the most stunning view and sunsets….close to all the great ocean beaches….an amazing outdoor shower….books, beach chairs, beach towels, beach games….you do not need to bring anything but a good relaxing vibe to this home! We had a great stay with seven adult family members! Wellfleet is just beautiful….can not wait to come back!

Stayed: June 2022 Submitted: June 27, 2022