Vienna House
Front Porch
Side Porch and Parking
Kitchen
Kitchen & island

Vienna Ave House

3 bedrooms·2 baths
Oak Bluffs • Massachusetts

$4,300.72 USD total for 6 nights

Oct 13 – 19, 2026

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)
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)
Living Room
Living Room (Game Cabinet; Dogs Beds on Top)
Front
Living Room
Living Room

'The Whale's Tail' ~ Dogs Welcome

3 bedrooms·2 baths
Yarmouth • Massachusetts
5(1 review)

$1,300.00 USD total for 3 nights

Oct 17 – 20, 2026

Little Elm Cottage image 1
Little Elm Cottage image 2
Little Elm Cottage image 3
Little Elm Cottage image 4
Little Elm Cottage image 5

Little Elm Cottage

2 bedrooms·1 bath
Dartmouth • Massachusetts
5(11 reviews)

$985.00 USD total for 3 nights

Oct 25 – 28, 2026

Sea Glenn Flowers
Full Kitchen
Primary Bedroom Suite 2nd Floor
Sea Glenn Flowers
Sea Glenn Flowers Vacation Home

Sea Glenn Flowers Vacation Home

4 bedrooms·3 baths
Oak Bluffs • Massachusetts

$1,943.62 USD total for 3 nights

Oct 13 – 16, 2026

Thompson House Cape Cod
Thompson House Cape Cod
Thompson House Cape Cod
Thompson House Cape Cod
Full kitchen

Thompson House Cape Cod

2 bedrooms·1 bath
Yarmouth • Massachusetts
3(2 reviews)

$3,815.69 USD total for 7 nights

Oct 13 – 20, 2026

Martha’s Vineyard Oasis, Hot Tub, Near It All!
Relax and unwind after a day at the beach or biking on the many bike paths.
Martha’s Vineyard Oasis, Hot Tub, Near It All!
Martha’s Vineyard Oasis, Hot Tub, Near It All!
Martha’s Vineyard Oasis, Hot Tub, Near It All!

Martha’s Vineyard Oasis, Hot Tub, Near It All!

3 bedrooms·2 baths
Tisbury • Massachusetts
4.9(21 reviews)

$2,075.50 USD total for 3 nights

Oct 13 – 16, 2026

Cozy island cottage with everything you need!
Bright and airy living area to put your feet up and relax. Sofa opens up into a queen sleeper for extra sleeping capacity.
Cozy up island cottage - Near everything!
Full size stack washer and dryer for your use. Detergent provided.
Enjoy fresh coffee by the cup using K-cups or the ground coffee K-cup adapter.

Cozy up island cottage - Near everything!

1 bedroom·1 bath
Tisbury • Massachusetts
4.86(21 reviews)

$1,587.05 USD total for 3 nights

Oct 13 – 16, 2026

Lovely Martha's Vineyard 3/2 Vacation Rental!
Lovely Martha's Vineyard 3/2 Vacation Rental!
Lovely Martha's Vineyard 3/2 Vacation Rental!
Lovely Martha's Vineyard 3/2 Vacation Rental!
Lovely Martha's Vineyard 3/2 Vacation Rental!

Lovely Martha's Vineyard 3/2 Vacation Rental!

3 bedrooms·2 baths
Edgartown • Massachusetts

$6,450.00 USD total for 6 nights

Oct 13 – 19, 2026

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

$1,160.37 USD total for 3 nights

Oct 13 – 16, 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 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

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

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)

$24,822.26 USD total for 7 nights

May 23 – 30, 2027

Outermost Penninsula w cottage to left
Main House
Outermost Penninsula view to Edgartown
Living Room fireplace
Super Moon Rising over Main House

Outermost House

6 bedrooms·5½ baths
Edgartown • Massachusetts

$15,801.11 USD $14,633.66 USD total for 7 nights

Oct 13 – 20, 2026

Entrance on North Water St
Main House from Pool House
Back Entrance to Main House
Back Patio
Kitchen

Connaught House Luxury North Water Street enclave with pool

6 bedrooms·5½ baths
Edgartown • Massachusetts

$31,754.08 USD total for 7 nights

Oct 17 – 24, 2026

The Captain Morse House
The Captain Morse House looking towards town
The Captain Morse House looking towards town
Back Pation
Large Lawn suitable for events

Captain Morse House

12 bedrooms·7 baths
Edgartown • Massachusetts
4.97(35 reviews)

$8,568.43 USD total for 3 nights

Oct 31 – Nov 3, 2026

West Wing of the Captain Morse House
West is on the Left - East is on the right
West Wing and lawn
West and East 8 person patio tables
Patio and Lawn

West Wing of the Captain Morse House

6 bedrooms·4 baths
Edgartown • Massachusetts

$4,849.12 USD total for 3 nights

Oct 31 – Nov 3, 2026

East Wing of the Captain Morse House
East Wing of the Captain Morse House
Front Door
Front Porch - 1st floor
View down Morse to the harbor

East Wing of the Captain Morse House

6 bedrooms·3 baths
Edgartown • Massachusetts

$5,332.62 USD total for 3 nights

Oct 21 – 24, 2026

View of Ferry House #2
2nd Floor Deck
Entryway, Stairwell Upstairs
Primary Bedroom
Primary Bedroom

Amazing waterfront home in Edgartown with Light House view

4 bedrooms·4 baths
Edgartown • Massachusetts

$25,426.27 USD total for 7 nights

Oct 18 – 25, 2026

Ferry House #4
Back entrance to Ferry House
Waterfront view from dock
Stairs to 2nd Floor
Great Room

Morse Ferry House - Deluxe waterfront home in Edgartown

3 bedrooms·3 baths
Edgartown • Massachusetts

$25,426.27 USD total for 7 nights

Oct 18 – 25, 2026

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

$949.62 USD total for 3 nights

Oct 25 – 28, 2026

Private deck, facing side street.
Front of building. Our unit is the whole third floor.
Water view
Spacious fully equipped eat-in kitchen
Living room facing the bay

Lovely, West End, Water Views, Spacious!

2 bedrooms·1 bath
Provincetown • Massachusetts
4.95(83 reviews)

$1,667.66 USD total for 3 nights

Nov 1 – 4, 2026