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

Vienna Ave House

3 bedrooms·2 baths
Oak Bluffs • Massachusetts

$2,855.50 USD total for 3 nights

Sep 23 – 26, 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

$2,509.48 USD total for 3 nights

Sep 23 – 26, 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)

$2,263.16 USD total for 3 nights

Sep 30 – Oct 3, 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)

$1,616.09 USD total for 3 nights

Sep 23 – 26, 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
$1,000/ 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)

$713.00 USD total for 3 nights

Oct 3 – 6, 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)
$3,000 – $4,000/ night(excl. fees & taxes)
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

$43,834.43 USD total for 7 nights

Sep 26 – Oct 3, 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)

$7,988.57 USD total for 3 nights

Sep 28 – Oct 1, 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

$4,577.30 USD total for 3 nights

Sep 28 – Oct 1, 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

$6,480.25 USD total for 3 nights

Sep 28 – Oct 1, 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

Sep 27 – Oct 4, 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

Sep 27 – Oct 4, 2026

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

$18,507.10 USD $17,123.18 USD total for 7 nights

Sep 23 – 30, 2026

Seas The Day image 1
Seas The Day image 2
fully stocked kitchen with microwave, dishwasher, keurig coffeemaker, toaster, blender, etc.
living room with cable TV
sunroom with washer/dryer.

Seas The Day

2 bedrooms·1 bath
Wareham • Massachusetts
4.92(66 reviews)
$265/ night(excl. fees & taxes)
View of Main House
Entrance off Driveway into Kitchen
Living Area
Living Area
Living Area

Sandpiper Fields Luxury Field Club Home close to South Beach

4 bedrooms·4½ baths
Edgartown • Massachusetts

$32,303.74 USD total for 7 nights

Sep 26 – Oct 3, 2026

Compound from Driveway
Walkway to Front door
Carriage House/Garage
Front Door
Pool

Sandcastle - Luxurious compound in the prestigious Field Club

5 bedrooms·5½ baths
Edgartown • Massachusetts

$49,874.61 USD total for 7 nights

Sep 26 – Oct 3, 2026

Welcome to Katama Delight of Martha's Vineyard
South facing sunny balconies and deck
Welcoming entry to our home, laundry area enclosed by glass doors (adjacent to the kitchen)
Cathedral ceiling great room; a bright and airy space with plentiful seating
Spacious and bright cathedral ceiling great room; sliding door to deck, lawn and garden

Katama Delight of Martha's Vineyard

4 bedrooms·3 baths
Edgartown • Massachusetts

$13,596.80 USD total for 7 nights

Sep 23 – 30, 2026

Welcome! The home has been family owned & loved since 1962. Lots of great memories have been shared here. I look forward to hosting you while you create your own special memories. Quick stroll to the
The popular West Island Town Beach is resident only BUT a beach pass comes with your reservation. Enjoy the quiet surf, views of the Elizabeth Islands, watch kite surfing, fishing boats, pleasure boat
Off Sconticut Neck, which is a pennisula, and within a short walking or driving distance are tiny beaches for your sunrise or sunset viewing.
Off Sconticut Neck, which is a pennisula, and within a short walking or driving distance are tiny beaches for your sunrise or sunset viewing.
Off Sconticut Neck, which is a pennisula, and within a short walking or driving distance are tiny beaches for your sunrise or sunset viewing.

Warm & Sunny All Year Round. Come Visit!

4 bedrooms·2 baths
Fairhaven • Massachusetts
4.73(75 reviews)

$1,032.75 USD total for 3 nights

Nov 8 – 11, 2026

Swifts Beach House
Swifts Beach House
Swifts Beach House
Swifts Beach House
Swifts Beach House

Swifts Beach House

4 bedrooms·1 bath
Wareham • Massachusetts
$249 – $449/ night(excl. fees & taxes)
Main House
Roses on the stone wall
Driveway
Garage Apt
Laundry

Katama Bay View Oyster Catcher

4 bedrooms·4 baths
Edgartown • Massachusetts

$19,673.72 USD total for 7 nights

Sep 26 – Oct 3, 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
$596 – $2,545/ night(excl. fees & taxes)
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)
The Freedom HOME from HOME
The Freedom HOME from HOME
The Freedom HOME from HOME
The Freedom HOME from HOME
The Freedom HOME from HOME

The Freedom HOME from HOME

3 bedrooms·1 bath
New Bedford • Massachusetts
4(1 review)
$195 – $220/ night(excl. fees & taxes)