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Dennis Vacation Rentals

(56 rentals)
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Walk to Private Beach in Dennisport
Walk to Private Beach in Dennisport

2 BR | 1 BA | Sleeps 5 | Quick View

Distance to beach: 200 yards to Longell Rd Beach

$279

avg/night

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Key Amenities

  • Kid friendly
  • Pet friendly

About this property

31 Longell Rd. Dennisport , PRIVATE BEACH 3/10 MILE AWAY ! A 2 bedroom 1 bath ( tub w/shower) cottage that sleeps 5 in an area of like cottages and walk to Private Longell Rd Beach Assoc. at the end of the road. There is an outside shower, stack-able washer/dryer, internet, cable, and a gas grille. Cute ...

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Property Type

Dennis Cottage

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Spacious Retreat
Spacious Retreat

3 BR | 2 BA | Sleeps 8 | Quick View

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Key Amenities

  • Kid friendly

About this property

Welcome to Hoppy’s Landing, a 3 bedroom, 2 bath, updated colonial with central air that easily sleeps 8. This beautiful, spacious home is centrally located mid Cape and situated on a quiet residential street, with a private backyard, along conservation land. You will feel like you are a world ...

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Property Type

Dennis House

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Newly Renovated Mid-Cape Home with Pond and Waterfront Access
Newly Renovated Mid-Cape Home with Pond and Waterfront Access

4 BR | 1.5 BA | Sleeps 11 | Quick View

$500

avg/night

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Key Amenities

  • Kid friendly

About this property

Welcome to our charming single-family house in South Dennis, Cape Cod, Massachusetts! This delightful retreat offers a cozy and comfortable setting for your vacation, with its four inviting bedrooms, one full bath, and a refreshing outdoor shower. Nestled in a serene neighborhood, this property provides ...

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Property Type

Dennis House

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Charming Cape Cod Home and Quaint Guest House.
Charming Cape Cod Home and Quaint Guest House.

5 BR | 2 BA | Sleeps 10 | Quick View

$526

avg/night

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About this property

Fantastic location, two blocks from Dennisport Village, where you will find restaurants, shopping, an ice cream shop, a playground, and the Village Green. It is a two-minute drive to the beach—a fun, large backyard featuring a bar, grill, fire pit, and picnic tables.

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Property Type

Dennis House

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By the Sea Guests Bed and Breakfast, Suites, and Houses
By the Sea Guests Bed and Breakfast, Suites, and Houses

19 BR | 1 BA | Sleeps 19 | Quick View

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Key Amenities

  • Beachfront
  • Kid friendly
  • Oceanfront
  • Rentals by owner

About this property

By the Sea Guests is a family-owned inn located in the heart of Dennis Port off of Chase Avenue and a close drive to the center of Dennis, Harwich Port, Chatham, Hyannis, and more where many of the shops and restaurants are.Beachfront, By the Sea Guests has the largest private beach on the strip ...

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Property Type

Dennis Apartment

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An English Garden Bed and Breakfast
An English Garden Bed and Breakfast

11 BR | 1 BA | Sleeps 14 | Quick View

Distance to beach: 500 feet to Inman Rd Beach

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Key Amenities

  • Beachfront
  • Kid friendly
  • Oceanfront
  • Rentals by owner

About this property

Formerly known as The Loydon Inn and the Innisfree, An English Garden Bed and Breakfast was built in 1922 and lovingly renovated in 1999. It’s one of the oldest bed and breakfasts in Dennis Port. The grey shingled cottage is surrounded by blooming English roses, hydrangea bushes and delphiniums ...

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Property Type

Dennis Apartment

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Dennis Vacation Rentals
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Find your perfect Dennis vacation rental today


Ready for an incredible vacation to the Cape this year? It's time forget booking a hotel and book one of our Dennis vacation rentals instead. We have great options throughout Dennis, including Dennis Port and East Dennis. The public beaches in this mid-Cape town can't be beat for a family-friendly trip. Dennis beaches line both the north side on Cape Cod Bay and its south side on Nantucket Sound. Vacation homes are the perfect option for your upcoming trip and for travelers looking in Dennis, we have you covered.

Dennis, Massachusetts travel advice


If you're looking for the best of what Cape Cod can offer from beaches to activities to location, then set your crosshairs on Dennis. Its handful of villages offer a diversity of experiences so make sure you research and are aware of the different areas. Despite the differences, you really can't go wrong with all the beaches and activities during the summer because they're all historic and they all have access to beaches, dining options, and great vacation rental options. Dennis Beach Parking (@DennisParking) on Twitter is worth a follow if you rent a Dennis vacation rental and want up-to-the-minute updates on beach parking.

The main throughway on the bayside is route 6a which is lined with shops and beach options. Route 134 runs north and south and connects all five villages including route 6 (major throughway) and route 28 which is on the south side and connects West Dennis and Dennis Port.

Top attractions and activities


Dennis touts itself as a "Play and Stay" destination and we have to agree!

Its access to trails and hiking includes the 22+ mile Cape Cod Rail Trail. And Dennis is where you'll find Bass River, which is the Cape's longest river. Adventure and activity awaits nature-loving travelers who stay in Dennis with everything from Kayaking on the Swan Pond River to the Indian Conservation Area in South Dennis.

The Cape is packed with historical relevance but perhaps more than any other town around, Dennis's history is a big draw with its many historic buildings spanning multiple centuries. The Jericho Historical Center (see here) and the 1801 Captain Baker house site on Old main street in West Dennis. It's only open June - September so apologies to you "shoulder season" travelers.

Dennis offers some of the best golf options around, too. Check out the Dennis Pines & Highlands Courses for some of the premier options when you vacation on the Cape.

Dennis is for the Arts! We'd be remiss if we left out the lovely 23-acre Cape Cod Center for the Arts (CCCArts) in Dennis. It features many options for entertainment for vacationers including the historic Cape Playhouse (more on that below!). The Cape Cod Museum of Art also calls Dennis home and has events and exhibitions to check out, and it stays open into the fall with its Artfull Thursday events.

Last but certainly not least, many vacation rentals orbit around Dennis great beaches, of which there are almost 20!

Dennis village features two of the most popular beaches: Corporation Beach and Mayflower Beach on the north/bayside. If tidal flats are your thing, consider a trip to Mayflower on Dunes Road. You won't be disappointed! While Dennisport to the south/Nantucket sound side features Sea Street and Haigis beaches among others. For parking and facilities/bathroom availability information, see this helpful page from the Dennis Chamber of Commerce for all the info you'll need. 

Summer events


Dennis Summerfest has been running for decades as a prime way to attract visitors during the last week of August (which is the end of the summer vacation rental season, traditionally). Events include bonfire on West Dennis Beach, local bands, a fireworks display, and an antique car parade.

Love the theater? The Cape Playhouse boasts high quality, professional live entertainment. Be sure to check out its Season Overview (here's the overview for 2020). It's among the oldest professional summer stock theatre in the United States and has been running continuously since 1927! According to their Facebook page, legends like Humphrey Bogart, Bette Davis, and Lana Turner have performed here.

The CCCArts, which is Dennis's Arts Center, offers "ImaginationStation - Theater for Children" twice a week on Thursdays and Fridays during July and August.

Great restaurants and bars


Dennis has some great spots for dining -- as evidence by the hundreds of reviews on Google and elsewhere. Scago Cafe in Dennis Village sets the pace on the bayside. It's joined by Encore Bistro and Bar on Hope Lane.

The Ocean House Restaurant in Dennis Port is where the expansive ocean views are a big part of experience. Its new American and pan-Asian menu is perfect fo a special dinner for a party of any size.

Want a local dining experience? Don't miss lunch or breakfast at Grumpy's in East Dennis. It's family-owned and operated and right on Main Street. But keep in mind: it opens early closes early (6am - 2pm).

Not exactly a newsflash, but ice cream is kind of a big deal for any Cape Cod vacation. Dennis has no shortage of options with the uber-popular Sundae School Ice Cream and up-and-coming Aunties' Ice Cream Parlor in Dennis Port, MA, and the can't be missed Ice Cream Smuggler in East Dennis Village.

Dennis vacation rentals on Cape Cod Vacation Rentals


Booking one of our vacation homes in Dennis on CapeCodVacationRentals.com can save you 20% or more over our competitors. And, we have a wide array of inventory for any group size or traveler tastes. Book yours today before someone else does!