Location

Dates

Guests

Vacation rentals in Massachusetts

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

$2,498.00 USD total for 3 nights

Oct 20 – 23, 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

Oct 20 – 27, 2026

Roses on the stone wall

Katama Bay View Oyster Catcher

4 bedrooms·4 baths

Edgartown • Massachusetts

$19,673.72 USD total for 7 nights

Oct 24 – 31, 2026

Compound from Driveway

Walkway to Front door

Carriage House/Garage

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

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

$20,223.38 USD total for 7 nights

Oct 24 – 31, 2026

Back entrance to Ferry House

Waterfront view from dock

Stairs to 2nd Floor

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

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

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 20 – 26, 2026

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

View of Vineyard Haven Sound from living room

View of Vineyard Haven Sound from deck

Aerial view of Cottage

Waterfront Cottage Martha’s Vineyard

2 bedrooms·1 bath

Oak Bluffs • Massachusetts

$1,500.00 USD total for 3 nights

Oct 20 – 23, 2026

Charming Beacon Hill 1bd in Brownstone

Charming Beacon Hill 1bd in Brownstone

Charming Beacon Hill 1bd in Brownstone

Charming Beacon Hill 1bd in Brownstone

Charming Beacon Hill 1bd in Brownstone

Charming Beacon Hill 1bd in Brownstone

1 bedroom·1 bath

Boston • Massachusetts

$1,002.00 USD total for 3 nights

Oct 23 – 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

$1,975.00 USD total for 3 nights

Oct 20 – 23, 2026

Carriage House

1 bedroom·1 bath

Sharon • Massachusetts

$1,550.00 USD total for 3 nights

Jan 1 – 4, 2027

Cedar Point/lighthouse/Oceanview (ocean across st) image 1

Cedar Point/lighthouse/Oceanview (ocean across st) image 2

Cedar Point/lighthouse/Oceanview (ocean across st) image 3

Cedar Point/lighthouse/Oceanview (ocean across st) image 4

Cedar Point/lighthouse/Oceanview (ocean across st) image 5

Cedar Point/lighthouse/Oceanview (ocean across st)

3 bedrooms·1 bath

Scituate • Massachusetts

5(2 reviews)

$1,594.31 USD total for 3 nights

Oct 20 – 23, 2026

Wood fireplace!

YourVacayHome

4 bedrooms·2½ baths

Upton • Massachusetts

$8,000.00 USD total for 3 nights

Oct 20 – 23, 2026

Casa Castor • Private Room 1

Casa Castor • Private Room 1

Casa Castor • Private Room 1

Casa Castor • Private Room 1

Casa Castor • Private Room 1

Casa Castor • Private Room 1

1 bedroom·1 bath

Chelsea • Massachusetts

$417.15 USD total for 3 nights

Oct 20 – 23, 2026

Casa Castor • Private Room 3

Casa Castor • Private Room 3

Casa Castor • Private Room 3

Casa Castor • Private Room 3

Casa Castor • Private Room 3

Casa Castor • Private Room 3

1 bedroom·1 bath

Chelsea • Massachusetts

$417.15 USD total for 3 nights

Oct 20 – 23, 2026

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

5 bedrooms·3 baths

Eastham • Massachusetts

$2,997.66 USD $2,742.89 USD total for 3 nights

Oct 25 – 28, 2026

Berkshires Cottage | Trails & Water Nearby

Berkshires Cottage | Trails & Water Nearby

Berkshires Cottage | Trails & Water Nearby

Berkshires Cottage | Trails & Water Nearby

Fully stocked eat-in kitchen

Berkshires Cottage | Trails & Water Nearby

2 bedrooms·1 bath

Monterey • Massachusetts

$521.55 USD total for 3 nights

Oct 20 – 23, 2026

Bright, cozy bedroom with storage bed and plenty of natural light

Casa Castor • Private Room 2

Casa Castor • Private Room 2

Casa Castor • Private Room 2

Casa Castor • Private Room 2

Casa Castor • Private Room 2

1 bedroom·1 bath

Chelsea • Massachusetts

$417.15 USD total for 3 nights

Oct 20 – 23, 2026

Jiminy Peak Slopeside Getaway • Ski & Adventure

Jiminy Peak Slopeside Getaway • Ski & Adventure

Jiminy Peak Slopeside Getaway • Ski & Adventure

Jiminy Peak Slopeside Getaway • Ski & Adventure

Jiminy Peak Slopeside Getaway • Ski & Adventure

Jiminy Peak Slopeside Getaway • Ski & Adventure

2 bedrooms·2 baths

Hancock • Massachusetts

$722.00 USD total for 3 nights

Oct 22 – 25, 2026

Second Bedroom through door in back of rv

Turnkey furnished luxury RV getaway

2 bedrooms·1½ baths

Danvers • Massachusetts

$700.00 USD $525.00 USD total for 7 nights

Oct 20 – 27, 2026

Calder 2

3 bedrooms·1 bath

Gloucester • Massachusetts

The Spot

1 bedroom·1 bath

Lawrence • Massachusetts

$180 – $200/ night(excl. fees & taxes)