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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

Cozy Coastal Retreat West Dennis - 13

Cozy Coastal Retreat West Dennis - 13

Cozy Coastal Retreat West Dennis - 13

Cozy Coastal Retreat West Dennis - 13

Cozy Coastal Retreat West Dennis - 13

Cozy Coastal Retreat West Dennis - 13

3 bedrooms·1 bath

Dennis • Massachusetts

Coastal Haven in West Dennis -15

Coastal Haven in West Dennis -15

Coastal Haven in West Dennis -15

Coastal Haven in West Dennis -15

Coastal Haven in West Dennis -15

Coastal Haven in West Dennis -15

3 bedrooms·1 bath

Dennis • Massachusetts

$1,307.55 USD total for 3 nights

Sep 22 – 25, 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

Luxury Getaway with Hot Tub!

Luxury Getaway with Hot Tub!

Luxury Getaway with Hot Tub!

Luxury Getaway with Hot Tub!

Luxury Getaway with Hot Tub!

Luxury Getaway with Hot Tub!

4 bedrooms·3 baths

Harwich • Massachusetts

$420 – $1,456/ night(excl. fees & taxes)

Spacious Retreat for Relaxation

Spacious Retreat for Relaxation

Spacious Retreat for Relaxation

Spacious Retreat for Relaxation

Spacious Retreat for Relaxation

Spacious Retreat for Relaxation

4 bedrooms·3 baths

Yarmouth • Massachusetts

$880.00 USD total for 3 nights

Sep 28 – Oct 1, 2026

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

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)

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

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)

Direct Ocean View Studio w/ 2 King Beds + Deck (201)

Direct Ocean View Studio w/ 2 King Beds + Deck (201)

Direct Ocean View Studio w/ 2 King Beds + Deck (201)

Direct Ocean View Studio w/ 2 King Beds + Deck (201)

Direct Ocean View Studio w/ 2 King Beds + Deck (201)

Direct Ocean View Studio w/ 2 King Beds + Deck (201)

0 bedrooms·1 bath

Falmouth • Massachusetts

$249 – $650/ night(excl. fees & taxes)

Partial Ocean View! 2 Queen Studio w/ Private Deck (312)

Partial Ocean View! 2 Queen Studio w/ Private Deck (312)

Partial Ocean View! 2 Queen Studio w/ Private Deck (312)

Partial Ocean View! 2 Queen Studio w/ Private Deck (312)

Partial Ocean View! 2 Queen Studio w/ Private Deck (312)

Partial Ocean View! 2 Queen Studio w/ Private Deck (312)

0 bedrooms·1 bath

Falmouth • Massachusetts

$219 – $575/ night(excl. fees & taxes)

Direct Ocean View Studio w/ 2 King Beds + Deck (201)

Direct Ocean View Studio w/ 2 King Beds + Deck (201)

Direct Ocean View Studio w/ 2 King Beds + Deck (201)

Direct Ocean View Studio w/ 2 King Beds + Deck (201)

Direct Ocean View Studio w/ 2 King Beds + Deck (201)

Direct Ocean View Studio w/ 2 King Beds + Deck (201)

0 bedrooms·1 bath

Falmouth • Massachusetts

$354 – $544/ night(excl. fees & taxes)

Partial Ocean View! 2 Queen Studio w/ Private Deck (312)

Partial Ocean View! 2 Queen Studio w/ Private Deck (312)

Partial Ocean View! 2 Queen Studio w/ Private Deck (312)

Partial Ocean View! 2 Queen Studio w/ Private Deck (312)

Partial Ocean View! 2 Queen Studio w/ Private Deck (312)

Partial Ocean View! 2 Queen Studio w/ Private Deck (312)

0 bedrooms·1 bath

Falmouth • Massachusetts

$294 – $474/ night(excl. fees & taxes)

Direct Ocean View Studio w/ 2 King Beds + Deck (201)

Direct Ocean View Studio w/ 2 King Beds + Deck (201)

Direct Ocean View Studio w/ 2 King Beds + Deck (201)

Direct Ocean View Studio w/ 2 King Beds + Deck (201)

Direct Ocean View Studio w/ 2 King Beds + Deck (201)

Direct Ocean View Studio w/ 2 King Beds + Deck (201)

0 bedrooms·1 bath

Falmouth • Massachusetts

$1,664.43 USD total for 3 nights

May 14 – 17, 2027

Partial Ocean View! 2 Queen Studio w/ Private Deck (312)

Partial Ocean View! 2 Queen Studio w/ Private Deck (312)

Partial Ocean View! 2 Queen Studio w/ Private Deck (312)

Partial Ocean View! 2 Queen Studio w/ Private Deck (312)

Partial Ocean View! 2 Queen Studio w/ Private Deck (312)

Partial Ocean View! 2 Queen Studio w/ Private Deck (312)

0 bedrooms·1 bath

Falmouth • Massachusetts

$1,375.58 USD total for 3 nights

May 14 – 17, 2027

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

View of Main House

Entrance off Driveway into Kitchen

Sandpiper Fields Luxury Field Club Home close to South Beach

4 bedrooms·4½ baths

Edgartown • Massachusetts

$1,643 – $6,631/ night(excl. fees & taxes)

Welcome to summer on Martha's Vineyard. We look forward to hosting you!

A long, tree‑lined shell drive leads to the home, creating a peaceful, private approach framed by mature trees.

Settle into the front‑porch swing and enjoy a peaceful moment with your morning coffee or a good book. A cozy, inviting spot to unwind and take in the day.

The barrel sauna creates a tranquil escape steps from the house. Perfect for relaxing after a long day.

A beautifully set spa offers a quiet place to soak and recharge, framed by gardens and the soft glow of natural light. There are two outdoor showers to use after the beach or to enjoy the outdoors!

Hidden Vineyard - 5bd, Heated Pool, Spa & Sauna

5 bedrooms·3½ baths

Edgartown • Massachusetts

5(31 reviews)

$32,875.83 USD total for 7 nights

Oct 1 – 8, 2026

Relaxing morning walks on Priscilla Beach! Nothing like it!

Large property with great privacy

Captain's Cottage in Priscilla Beach

Updated kitchen with quartz counter tops, stainless steel appliances and beach-wood style tile floors.

NEW kitchen withttps://app.guesty.com/reservationsh quartz counter tops, stainless steel appliances and beach-wood style tile floors.

Beautiful PriscillaBeach Few Min. Walk to Beach!

2 bedrooms·1 bath

Plymouth • Massachusetts

4.81(36 reviews)

$1,172.85 USD total for 3 nights

Sep 22 – 25, 2026