Dennis Port Holiday Rentals, Massachusetts: Private House Rentals

A beach house with a sandy path leading to it, surrounded by grass and overlooking the ocean.

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Go beyond your typical stay in Dennis Port

Pet friendly

Pool

Apartment

Condo

Hot tub

Apart hotel

Spa

Cottage

Family friendly

Waterpark

Check prices for these dates

Tonight

Tomorrow

This weekend

Next weekend

Our top choices for Dennis Port hotels

An outdoor seating area with a fire feature, a pool, and a view of the ocean.

A bedroom with a large bed, two armchairs, a small table, and a view of the sea through large windows.

A beach with a modern building, a staircase, and a rocky shoreline.

A pool area with lounge chairs and a table, overlooking the ocean.

1. Pelham House Resort

Dennis Port

sandra

6.694.114 ₫

8.427.347 ₫ total

includes taxes & fees

3 Nov - 4 Nov

A plate of French toast with bananas on a beach view.

A bedroom with a view of the beach through a window, a small table with a plant, and a bed with white linens.

A beach house with a white exterior, two large windows, and a view of the ocean at sunset.

A bedroom with a view of the ocean through a window, a bedside table with a plant, and a bed with white bedding.

2. By the Sea Guests Bed & Breakfast & Suites

Dennis Port

Vincent

5.830.791 ₫

7.413.431 ₫ total

includes taxes & fees

24 Oct - 25 Oct

A two-story house with a white picket fence, a blue door, and a porch with white railings.

A residential building with a white picket fence, a mailbox, and a variety of flowering plants.

A dining area with floral tablecloths, white chairs, and a wooden floor.

A living room with a sofa, two armchairs, a glass coffee table, and a rug.

3. An English Garden Bed & Breakfast

Dennis Port

Donna M.

4.975.613 ₫

6.434.108 ₫ total

includes taxes & fees

6 Nov - 7 Nov

A motel with a swimming pool, parking lot, and a small gazebo.

A bedroom with a large bed, a TV mounted on the wall, and a skylight.

A living room with a fireplace, a television displaying a nature scene, and a dining area with a table and chairs.

A swimming pool with a wooden deck and a covered seating area with string lights.

4. Jonathan Edwards Motel

Dennis Port

Katerin

2.770.249 ₫

3.170.549 ₫ total

includes taxes & fees

25 Oct - 26 Oct

A two-story house with a front porch, a mailbox, and a well-maintained garden.

A modern interior with a wooden floor, a blue and white patterned wall, a large painting, and a bar area with a blue marble backsplash.

A swimming pool with lounge chairs and a covered seating area.

A covered porch with white Adirondack chairs, a trash can, and a door marked with the number 9.

5. Pelham on Earle

West Harwich

Colleen

4.884.894 ₫

6.037.884 ₫ total

includes taxes & fees

26 Oct - 27 Oct

A large, multi-story beachfront hotel with a prominent balcony and multiple windows.

A beachfront property with a large building, a sandy beach, and a rocky shoreline.

A clear swimming pool with blue chairs and umbrellas, a building with blue shutters, and a clear sky.

A grassy area with a building in the background, a flag, and several parked cars.

6. Lighthouse Inn

West Dennis

Megan

8.569.148 ₫

9.807.389 ₫ total

includes taxes & fees

24 Oct - 25 Oct

A room with nautical-themed decor, including a map, anchor-patterned rug, and a view of the sea through the window.

A hotel room with a bed, a desk, a chair, a television, a microwave, and a dresser.

A Beach Breeze Inn sign with a lighthouse graphic, a vacancy sign, and a building with a brick flower bed in front.

A clear blue swimming pool with a metal ladder, surrounded by lounge chairs and an American flag.

7. A Beach Breeze Inn

West Harwich

William

3.334.134 ₫

3.815.903 ₫ total

includes taxes & fees

25 Oct - 26 Oct

A modern hotel room with a kitchenette, a bed with a grey headboard, a grey sofa, and a view of the outdoors through a sliding door.

A modern living room with a sofa, two armchairs, a coffee table, and a side table. There is a large mirror on the wall, a window with curtains, and a door leading outside.

A backyard with a swimming pool, a stone pathway, and a white fence.

A covered balcony with a white railing, grey siding, and a glass door leading to the interior.

8. Love Farms Lodge

West Dennis

Todd

10.490.891 ₫

12.967.196 ₫ total

includes taxes & fees

24 Oct - 25 Oct

A pathway flanked by vibrant flowers and greenery, leading to a house with large windows.

A traditional house with a garden pathway leading to the entrance, surrounded by lush greenery and a white picket fence.

A deck with outdoor furniture, a large umbrella, and a view of a garden with flowers and a tree.

A living room with a sofa, a chair, a television, and a hallway leading to another room.

9. The Villa Callo Inn

West Harwich

Shawn

10.855.320 ₫

13.902.951 ₫ total

includes taxes & fees

24 Oct - 25 Oct

A two-story building with a sign for 'Ambassador Inn & Suites'.

A reception area with a wooden counter, a red mat, and a painting of a bridge.

An indoor swimming pool with clear water, surrounded by wooden walls and a lifebuoy on the wall.

A hotel with a row of windows, a parking lot, and a garden with marigold flowers.

10. Ambassador Inn & Suites

Bass River

Kevin

3.437.260 ₫

4.153.635 ₫ total

includes taxes & fees

26 Oct - 27 Oct

A hotel with a white facade, a covered outdoor seating area with white chairs and tables, and a view of the sunset.

A nighttime pool area with lounge chairs and a lifebuoy.

A sign for the Escape Inn Hotel with the address 1237.

A spacious dining area with white chairs and a marble table, a staircase, and a TV in the background.

11. The Escape Inn

Bass River

Marcegui

2.320.195 ₫

2.655.676 ₫ total

includes taxes & fees

1 Nov - 2 Nov

A two-story residential building with a well-maintained lawn, a wooden fence, and a patio area with outdoor furniture.

A cozy living room with a fireplace, striped sofa, wooden flooring, and exposed beams.

A modern bathroom with a glass shower enclosure, a white sink, and a towel rack.

A beach with clear water, a sandy shore, and houses in the background.

12. Kingfisher Harwich Port

Harwich Port

Marc

A hotel room with a large bed, a small table with chairs, a green armchair, a dresser, and a balcony with a view of trees.

A row of white, two-story buildings with a white fence in front, likely a motel or small hotel.

A hotel room with two beds, a sofa, a desk, and a window with curtains.

A sign for Blue Rock Golf Course surrounded by a variety of colorful flowers.

13. Blue Rock Resort

South Yarmouth

Camille

2.452.873 ₫

2.835.690 ₫ total

includes taxes & fees

26 Oct - 27 Oct

An indoor swimming pool with a clear view of the outside, a wooden wall with greenery, and a seating area with chairs.

A spacious lobby with a brick fireplace, seating area, and a large window providing natural light.

A two-story building with a black awning reading "AllSeasons Resort on Cape Cod."

A gym with various exercise equipment, large windows, and a view of the outside.

14. All Seasons Resort, Trademark Collection by Wyndham

Bass River

Dilma

2.442.447 ₫

3.105.655 ₫ total

includes taxes & fees

1 Nov - 2 Nov

A multi-story building with outdoor seating areas and a view of the sea.

A beach with a sandy path leading to the water, a row of chairs along the edge, and a grassy area in the foreground.

A coastal hotel with a pool, beach chairs, and a parking lot.

A hot tub with lounge chairs and candles, surrounded by a fence and overlooking a body of water.

15. Ocean Mist Beach Hotel & Suites

Bass River

Donna

5.208.895 ₫

6.612.887 ₫ total

includes taxes & fees

24 Oct - 25 Oct

A two-story house with a porch, surrounded by well-maintained gardens and trees.

A porch with white chairs and a planter with flowers.

A bedroom with a four-poster bed, a television on a wooden cabinet, a plant, and a tray with glasses and a bottle.

A dining area with a checkered floor, white tables, and chairs. There are bookshelves with books and decorative items.

16. The Captain Farris House B&B

Bass River

Ruth Ann

A balcony with a view of a beach, a table with a vase of flowers, and a chair.

Two blue Adirondack chairs facing a sunset over a beach with a fence and vegetation in the foreground.

A room with large windows overlooking a beach, a table with a bottle and glasses, and a chair.

A two-story building with a sign reading "Winston Inn and Boardwalk."

17. Winstead Beach Resort

Harwich Port

William

A room with a bed, two wicker chairs, a small table, a coffee maker, and a view of the sea through a window.

A white bicycle with brown tires parked outside a building with a wooden exterior.

A beachfront property with a wooden deck, a sign labeled "SHOWER," and surfboards stored outside.

A modern kitchen with white cabinets, a built-in oven, and a view of the ocean through large windows.

18. Chatham Tides

South Chatham

Chad

4.163.791 ₫

4.765.458 ₫ total

includes taxes & fees

17 Nov - 18 Nov

A pool area with lounge chairs and umbrellas, a diving board, and a view of the ocean.

A patio area with wicker furniture, a fire pit, and a view of the sea.

A beach with rows of sun loungers and a building with a sloped roof.

A room with a view of a dock and water, a table with a patterned tablecloth, and a hanging pendant light.

19. Red Jacket Beach Resort

Bass River

Eric

3.592.594 ₫

4.564.013 ₫ total

includes taxes & fees

29 Oct - 30 Oct

A sign for Handkerchief Shoals Inn with a well-maintained garden in the foreground.

A reception area with a counter, a blue door labeled "Office," and a wall-mounted shelf with various items.

A blue door labeled "Office" with a small window and a mailbox.

An outdoor patio with round tables and chairs, picnic tables, and umbrellas.

20. Handkerchief Shoals Inn

South Harwich

Matthew

4.609.321 ₫

5.275.371 ₫ total

includes taxes & fees

4 Nov - 5 Nov

View all properties

Save an average of 15% on thousands of hotels when you're signed in

Stay near popular Dennis Port attractions

An aerial view of a coastal town with a beach, houses, and a bay.

Sea Street Beach

8.6/10 (122 reviews)

Sea Street Beach charms with warm Nantucket Sound waters and gentle surf perfect for families. Enjoy the picturesque jetties and lifeguarded swimming while the convenient snack bar keeps you refreshed.

See properties

A white swan swimming in calm blue water.

Swan Pond River

8.4/10 (55 reviews)

This tranquil tidal estuary connects Swan Pond to Nantucket Sound with gentle waters perfect for kayaking. Paddle among reeds and diverse birdlife while enjoying the serene natural landscape away from coastal crowds.

See properties

Cape Cod Theatre Company – Home of the Harwich Jr. Theatre

7.6/10 (29 reviews)

Cape Cod Theatre Company stages multi-generational performances in an intimate, air-conditioned venue. Enjoy evening shows featuring both seasoned actors and emerging talents in this community-centered arts space.

See properties

Swan Pond

Commune with nature and explore the great outdoors at Swan Pond during your travels in Dennis Port. Wander the area's beautiful beaches or simply enjoy one of its top-notch restaurants.

See properties

Haigis Beach

7.8/10 (29 reviews)

Why not spend a lazy afternoon at Haigis Beach during your trip to Dennis Port? Wander the beautiful beaches and seaside in the area.

See properties

Learn more about Dennis Port

Stroll along Sea Street Beach, where soft sand meets gentle waves perfect for swimming and sunbathing. Explore charming local shops and seafood restaurants, or catch a show at the Cape Cod Melody Tent in nearby Hyannis.

See all hotels in Dennis Port

Top Dennis Port Hotel Reviews

Dennis Port Surf Club (Boutique Hotel)

8/10 Good

"Completely updated older hotel. Everything was spotless. The room was nice with an excellent king size mattress. Very comfortable. Because it was older architecture the bathroom was pretty small. Small sink and standard size bathtub with shower. And there was no outlet in the bathroom. Apparently, they said they were going to be doing some updates to that in the winter for next season. They had a nice pool and fire pit. It’s on the main drag of Route 28 but it was quiet there. Of course we were there in October so not high season. Convenient location to everything the Cape has to offer."

Sea Shell Motel

10/10 Excellent

"Our stay was wonderful. We went in October so everything was pretty quiet in the area. Our room was on the small side but everything was so clean! Very impressed with the quality of product provIded in the room (shampoo, soap and toilet paper). Beds were extremely comfortable and bedding so fresh. We were very impressed! Oh did I mention that our room opened up to the best oceanfront view? Right on the water with our own ground level porch just steps from the beach! Have already booked for next year!"

By the Sea Guests Bed & Breakfast & Suites

10/10 Excellent

"Wonderful stay. Enjoyed the beach. Great breakfast. Great staff. Seemed well run."

Jonathan Edwards Motel

8/10 Good

"Visited off season, but looks like the pool would be a draw. Excellent bed."

Doryman Motel

10/10 Excellent

"great stay"

An English Garden Bed & Breakfast

10/10 Excellent

"Wonderful stay!"

Pelham House Resort

10/10 Excellent

"The room was beautiful! Highly recommend!"

Kingfisher Oceanside

8/10 Good

"Very clean room. Super close to beach. Great check-in and room lock entry. Great office contact efforts and great they extended us early check-in. But no table and chairs to enable bringing in food to eat. A/C unit was loud. Bed pillows were like rocks. No outlet near bed so difficult to charge phone and have it nearby at night. Lighting was either super bright or very low. Room could be stuffy without a/c. We had to put out trash and laundry instead of housekeeping doing it. TV controller was ancient."

Bluegreen Vacations The Soundings, an Ascend Collection Resort

10/10 Excellent

"Everything at this hotel is what I want in a beachside resort. Easy access to the beach, outdoor pool, inside pool and outside hot tub. Kitchenette and fireplace. This was my 3rd stay and I will be back."