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Vacation rentals in Dennis Port

Living room with plenty of windows/light! Smart TV and some games/books.

Smart TV in the living room. Please bring your own passwords.

Cape Cod Romantic Getaway *Walk to Beach, Fire Pit

Bedroom with Queen bed, charging ports, dressers Smart TV and electric wall fireplace (not shown). We also changed out the fabric headboard to non-fabric.

Full bathroom with shower (there’s also an outdoor shower).

Cape Cod Romantic Getaway *Walk to Beach, Fire Pit

1 bedroom·1 bath

Dennis • Massachusetts

$2,203.17 USD total for 7 nights

Dec 23 – 30, 2026

Coastal Cape Cod Cottage Charm. Unwind after a long day at the beach and sightseeing - comfortable seating and smart TV.

Thoughtfully curated with amenities that will leave you feeling relaxed with everything you need and more!

Dining for 4 both inside and out (picnic table with umbrella) with cooking supplies for making meals on the stove, in the oven or on the grill!

Beach Grass Cottage has been totally remodeled with guest comfort in mind!

Kitchen has stove, oven, microwave, fridge/freezer, coffee maker, and kitchen items to cook either inside our out!

Cape Cod Beachgrass Cottage - Walk to Beach+ !!

2 bedrooms·1 bath

Dennis • Massachusetts

5(6 reviews)

$1,001.44 USD total for 3 nights

Dec 23 – 26, 2026

2 minute Walk to beach and town (from our quiet dead-end road) through charming "Campground" neighborhood

Easy stroll to the warm waters of Nantucket Sound beach

Awesome beach at the end of the street!

Pottery Barn Kitchen table seats six

The Breakfast bar raea seats 4

Harwichport Walk to Beach & Town

4 bedrooms·2½ baths

Harwich • Massachusetts

5(6 reviews)

$2,806.48 USD total for 3 nights

Sep 27 – 30, 2026

Game room with shuffle board, ski ball, air hockey and ping pong

Living Room and the Entertainment Center contains books, puzzles board games, smart television, and a robust record collection.

Epic Game Room - shuffleboard, airhockey, foosball, ping pong, xbox, wii and much more.......

Kitchen and Dining Area - Perfect for family and friend gatherings. Our favorite is to play board games at the table while friends watch the Bruins, Patriot's or Red Sox games at the TV in the living room!

* Game Room, Linens, Quiet St, Central AC/Heat

4 bedrooms·2 baths

Harwich • Massachusetts

5(343 reviews)

$970.94 USD total for 3 nights

Sep 27 – 30, 2026

Thompson House Cape Cod

Thompson House Cape Cod

Thompson House Cape Cod

Thompson House Cape Cod

Thompson House Cape Cod

2 bedrooms·1 bath

Yarmouth • Massachusetts

3(2 reviews)

$3,815.69 USD total for 7 nights

Sep 22 – 29, 2026

Fully equipped kitchen with island seating

Kitchen opens to bright dining area

Fenced-in backyard

Living room with seating for the whole group

'The Whales Tale' ~ Dogs Welcome

3 bedrooms·2 baths

Yarmouth • Massachusetts

$3,500.00 USD total for 7 nights

Jun 27 – Jul 4, 2027

Bright living room with fireplace, big windows, and easy backyard access

Bright, airy living room with big windows and cozy seating

Deeded beach rights to a private beach located several minutes away

Bright modern living room with comfy seating and large TV

Bright modern kitchen with stainless appliances and sunny window

Dennis Beach House - Walk to Beach - Pet Friendly

2 bedrooms·1 bath

Dennis • Massachusetts

4.74(132 reviews)

Ample backyard seating

Outdoor patio with seating area

Swan Pond is located within 0.5 miles from the house or 10 minutes walk!

Front of the house with a driveway that accommodates 2 cars

Kids are having so much fun at Swan Pond. 10 mins walk from the house.

Great Location, Yarmouth Beaches, Fenced-in yard!

2 bedrooms·1 bath

Yarmouth • Massachusetts

$180/ night(excl. fees & taxes)

Fully Renovated 3-Bedrooms 2-Baths W/En-suite.

Fully Renovated 3-Bedrooms 2-Baths W/En-suite.

Fully Renovated 3-Bedrooms 2-Baths W/En-suite.

Fully Renovated 3-Bedrooms 2-Baths W/En-suite.

Fully Renovated 3-Bedrooms 2-Baths W/En-suite.

Fully Renovated 3-Bedrooms 2-Baths W/En-suite.

3 bedrooms·2 baths

Yarmouth • Massachusetts

$250/ night(excl. fees & taxes)

Cape Cod Coastal Cottage Charm meets modern conveniences. Indulge yourself!

Kitchen has been completely redone and is fully stocked. Granite countertops, gas stove/oven, brisker, toaster oven, coffee maker, Keurig, french press, coffee bean grinder, grilling tools, pots/pans, basic spices, non-stick spray, etc.

Cape Cod Coastal Cottage Decor - be tastefully surrounded with the reason you are here! The Beach!

Cape Cod Coastal Cottage Decor - be tastefully surrounded with the reason you are here! The Beach!

Enclosed outdoor shower with hot/cold water.

Cape Cod Seagrass Cottage: Walk to Beach+Amenities

2 bedrooms·1 bath

Yarmouth • Massachusetts

5(1 review)

$3,422.06 USD total for 7 nights

Dec 23 – 30, 2026

PRIVATE BEACH Bay views image 1

Comfortable cottage with bay views on a private beach.

PRIVATE BEACH Bay views image 3

The view from your cottage. Bay views and Sunsets over the water.

Your private beach looking west

PRIVATE BEACH Bay views

2 bedrooms·1 bath

Brewster • Massachusetts

4.98(87 reviews)

$2,350.00 USD total for 4 nights

Sep 22 – 26, 2026

Luxurious Villa in the heart of Capecod

Luxurious Villa in the heart of Capecod

Luxurious Villa in the heart of Capecod

Luxurious Villa in the heart of Capecod

Luxurious Villa in the heart of Capecod

Luxurious Villa in the heart of Capecod

5 bedrooms·5 baths

Barnstable • Massachusetts

$3,136.00 USD total for 3 nights

Sep 22 – 25, 2026

Charming Family-Friendly, 3+ Bedroom, Farmhouse

Sunny kitchen with water filter on fridge and new stove in 2022. See other photos for close up of the new stove.

Charming Family-Friendly, 3+ Bedroom, Farmhouse

Bertazzoni gas range and electric oven installed in 2022 with superfast boil and pizza setting on the oven.

Sunny bright cook's kitchen is a delight to use. You'll find spices, gadgets, Kitchenaid mixer, blenders etc. New Bertazzoni gas range ‘22

Charming Family-Friendly, 3+ Bedroom, Farmhouse

4 bedrooms·2 baths

Orleans • Massachusetts

4.97(39 reviews)

$3,783.50 USD total for 4 nights

Sep 22 – 26, 2026

Beautiful Home Close to National Seashore Beaches!

Well-appointed kitchen is bright and welcoming

Decor is clean, cozy, and calming for a pleasant time away!

Plenty of comfortable seats for the family to gather and relax.

Comfortable and calming first floor bedroom with queen bed.

Beautiful Home Close to National Seashore Beaches!

4 bedrooms·2½ baths

Eastham • Massachusetts

$1,265.06 USD total for 3 nights

Oct 1 – 4, 2026

Brand New Luxury Home: Private Outdoor Oasis, Hot Tub, Sauna

5 bedrooms·3 baths

Eastham • Massachusetts

$609 – $2,257/ night(excl. fees & taxes)

Charming exterior with lush greenery and welcoming lighting, your Cape Cod vacation haven from the moment you arrive.

Second-floor bathroom with a full bathtub and fresh towels, perfect for relaxing soaks after a day exploring Cape Cod.

Bright and spacious living room with plush seating and natural light, perfect for relaxing, family gatherings, or cozy nights during your Cape Cod getaway.

Cape Cod Getaway - 3BR/2BA Beach Pass Included

Cape Cod Getaway - 3BR/2BA Beach Pass Included

Cape Cod Getaway - 3BR/2BA Beach Pass Included

3 bedrooms·2 baths

Barnstable • Massachusetts

4.89(150 reviews)

$129 – $562/ night(excl. fees & taxes)

Deck, Bbq Grill, & Porch

WALK to WELLFLEET’s INDIAN NECK BEACH

3 bedrooms·2 baths

Wellfleet • Massachusetts

$275/ night(excl. fees & taxes)

Maushop Village Cottage

Maushop Village Cottage

Maushop Village Cottage

Maushop Village Cottage

Maushop Village Cottage

Maushop Village Cottage

2 bedrooms·1½ baths

Mashpee • Massachusetts

$4,800.00 USD total for 7 nights

Sep 22 – 29, 2026

Beautiful, inviting, and classic but modern.

Chef's kitchen, fully equipped. Gas stove.

Comfortable communal dining.

Dining outdoors, either on the deck or at the firepit.

The Map House - Modern Wellfleet Vacation

3 bedrooms·2 baths

Wellfleet • Massachusetts

5(3 reviews)

$1,230.34 USD total for 3 nights

Sep 27 – 30, 2026

Back of house, private deck & wooded property

Teak dining table with umbrella

Gorgeous Cape with Deck Close to Ponds and Ocean

3 bedrooms·2 baths

Wellfleet • Massachusetts

$3,614.63 USD total for 7 nights

Sep 22 – 29, 2026

New mid century modern style furniture with oceanfront views from the living room

Oceanfront cottage on a private beach

Your own private path to the beach

You can't get any closer to the your own private beach!

Beach chairs are provided! Ready for you to step out of your car and right onto the beach! No parking worries, always cold beverages and quick access to your own bathroom. A++ Beach towels are not provided.

Sand Castle Drive ~ Oceanfront with Private Beach

2 bedrooms·1 bath

Sandwich • Massachusetts

4.93(28 reviews)

$406/ night(excl. fees & taxes)

Outermost Penninsula w cottage to left

Outermost Penninsula view to Edgartown

Living Room fireplace

Super Moon Rising over Main House

Outermost House

6 bedrooms·5½ baths

Edgartown • Massachusetts

$1,407 – $3,413/ night(excl. fees & taxes)

Falmouth Heights Cottage

Falmouth Heights Beach

Fenced yard for dogs, kids, and family parties

Falmouth Heights Cottage ~ Cape Cod

3 bedrooms·2 baths

Falmouth • Massachusetts

5(68 reviews)

$3,116.47 USD total for 7 nights

Sep 27 – Oct 4, 2026

Beautiful view of Ocean Park and the Pavilion from the 2nd floor public balcony.

Living room with spectacular views of Ocean Park and the beach beyond.

Heart of Oak Bluffs, Ocean Views, Walk Everywhere!

Fully equipped kitchen.

Master bedroom with king bed and private balcony overlooking Ocean Park with breathtaking ocean views.

Heart of Oak Bluffs, Ocean Views, Walk Everywhere!

2 bedrooms·1 bath

Oak Bluffs • Massachusetts

5(6 reviews)

$2,313.10 USD total for 3 nights

Sep 22 – 25, 2026