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 24 – 31, 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 25 – Nov 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

Oct 25 – Nov 1, 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 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

$20,223.38 USD total for 7 nights

Oct 24 – 31, 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

Oct 24 – 31, 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

Oct 21 – 28, 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

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

Oct 24 – 31, 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

$15,233.33 USD $14,111.31 USD total for 7 nights

Oct 19 – 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

$6,450.00 USD total for 6 nights

Oct 19 – 25, 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)

$1,978.00 USD total for 3 nights

Oct 19 – 22, 2026

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

Vienna Ave House

3 bedrooms·2 baths
Oak Bluffs • Massachusetts

$2,253.33 USD total for 3 nights

Oct 19 – 22, 2026

Entrance
Sun Room
Front Entrance Spring 2025
Sunroom entrance
Kitchen

Holly Tree Haven

3 bedrooms·1 bath
Oak Bluffs • Massachusetts

$3,258.45 USD total for 5 nights

Jul 30 – Aug 4, 2027

Inca Gardens Patio with deck in background
Inca Gardens from the street
Entrance to deck and front door
Inca Gardens front entrance
Inca Gardens front deck

Inca Gardens Apartment in Oak Bluffs

3 bedrooms·1 bath
Oak Bluffs • Massachusetts
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

$2,052.22 USD total for 3 nights

Oct 19 – 22, 2026

View of Vineyard Haven Sound from living room
View of Vineyard Haven Sound from deck
Aerial view of Cottage
Front entrance
Kitchen

Waterfront Cottage Martha’s Vineyard

2 bedrooms·1 bath
Oak Bluffs • Massachusetts

$1,500.00 USD total for 3 nights

Oct 19 – 22, 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 19 – 22, 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)

$1,506.63 USD total for 3 nights

May 1 – 4, 2027

Falmouth Heights Cottage
Falmouth Heights Beach
Fenced yard for dogs, kids, and family parties
Outdoor shower
Kitchen

Falmouth Heights Cottage ~ Cape Cod

3 bedrooms·2 baths
Falmouth • Massachusetts
5(68 reviews)

$3,116.47 USD total for 7 nights

Oct 19 – 26, 2026

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

Oct 19 – 26, 2026

Quissett Landing | Sleeps 12 | Walk to The Knob
Historic home with wrap around deck on 1/4 acre.
Quissett Landing | Sleeps 12 | Walk to The Knob
Quissett Landing | Sleeps 12 | Walk to The Knob
Quissett Landing | Sleeps 12 | Walk to The Knob

Quissett Landing | Sleeps 12 | Walk to The Knob

4 bedrooms·2 baths
Falmouth • Massachusetts

$1,974.00 USD total for 3 nights

Oct 19 – 22, 2026