Location

Dates

Guests

Vacation rentals in Massachusetts

The Blooming Inn Front elevation summer view

Bridge of Flowers winter evening

Rose room Victorian home queen bed private bath

Rose room Victorian home queen bed private bath

Rose room Victorian home queen bed private bath

Rose room Victorian home queen bed private bath

1 bedroom·1 bath

Shelburne Falls • Massachusetts

4.8(5 reviews)

$466.80 USD total for 3 nights

Oct 25 – 28, 2026

Lovely Two Bedroom Condo in South Boston

Lovely Two Bedroom Condo in South Boston

Lovely Two Bedroom Condo in South Boston

Lovely Two Bedroom Condo in South Boston

Lovely Two Bedroom Condo in South Boston

Lovely Two Bedroom Condo in South Boston

2 bedrooms·1 bath

Boston • Massachusetts

$1,819.78 USD total for 3 nights

Oct 27 – 30, 2026

living and dining area

First floor full bathroom

Boston Historical Urban Oasis

7 bedrooms·3 baths

Boston • Massachusetts

$2,347.89 USD total for 3 nights

Nov 3 – 6, 2026

Enchanting Hidden Door Escape

4 bedrooms·2 baths

Stoneham • Massachusetts

$1,342.31 USD total for 3 nights

Oct 25 – 28, 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

WaterAccess 5-Bed 2-Bath Retreat

WaterAccess 5-Bed 2-Bath Retreat

WaterAccess 5-Bed 2-Bath Retreat

WaterAccess 5-Bed 2-Bath Retreat

WaterAccess 5-Bed 2-Bath Retreat

WaterAccess 5-Bed 2-Bath Retreat

5 bedrooms·2 baths

Barnstable • Massachusetts

$2,152.15 USD total for 3 nights

Oct 20 – 23, 2026

Charming Hyannis 3 Bed 2 Bath

Charming Hyannis 3 Bed 2 Bath

Charming Hyannis 3 Bed 2 Bath

Charming Hyannis 3 Bed 2 Bath

Charming Hyannis 3 Bed 2 Bath

Charming Hyannis 3 Bed 2 Bath

3 bedrooms·2 baths

Barnstable • Massachusetts

$1,419.69 USD total for 3 nights

Oct 20 – 23, 2026

Living Room
(Game Cabinet; Dogs Beds on Top)

'The Whale's Tail' ~ Dogs Welcome

3 bedrooms·2 baths

Yarmouth • Massachusetts

5(1 review)

$1,300.00 USD total for 3 nights

Oct 19 – 22, 2026

Modern Three Bedroom Condo - Near Boston

Modern Three Bedroom Condo - Near Boston

Modern Three Bedroom Condo - Near Boston

Modern Three Bedroom Condo - Near Boston

Modern Three Bedroom Condo - Near Boston

Modern Three Bedroom Condo - Near Boston

3 bedrooms·1 bath

Stoneham • Massachusetts

$1,217.50 USD total for 3 nights

Oct 20 – 23, 2026

Queen Bed |Boston|RM 3

Queen Bed |Boston|RM 3

Queen Bed |Boston|RM 3

Queen Bed |Boston|RM 3

Queen Bed |Boston|RM 3

Queen Bed |Boston|RM 3

1 bedroom·1 bath

Stoneham • Massachusetts

$330.80 USD total for 3 nights

Oct 20 – 23, 2026

Bedroom on the second floor with a queen bed

Front view of the home

Walk to the kitchen

Wide kitchen shot

Queen Bed |Boston|RM 2

1 bedroom·2 baths

Stoneham • Massachusetts

$379.95 USD total for 3 nights

Oct 26 – 29, 2026

Twin XL Bed|Boston|RM 1

Twin XL Bed|Boston|RM 1

Twin XL Bed|Boston|RM 1

Twin XL Bed|Boston|RM 1

Twin XL Bed|Boston|RM 1

Twin XL Bed|Boston|RM 1

1 bedroom·1 bath

Stoneham • Massachusetts

$399.87 USD total for 3 nights

Oct 20 – 23, 2026

The Blooming Inn Front elevation summer view

Marigold queen bed with en-suite bathroom

Marigold queen bed with en-suite bathroom

Private bed with En-suite bathroom Marigold Room

Private bed with En-suite bathroom Marigold Room

1 bedroom·1 bath

Shelburne Falls • Massachusetts

4.5(2 reviews)

$470.30 USD total for 3 nights

Oct 26 – 29, 2026

Sunny 1st floor unit with views

Smart TV in living room for streaming

Leather arm chairs

The Orca

2 bedrooms·1 bath

Rockport • Massachusetts

5(11 reviews)

$723.01 USD total for 3 nights

Nov 3 – 6, 2026

Living Room: Bright space with nautical charm, leather couch, and dining for four! Perfect for relaxing!

Living Room: Relax in style with plush seating, vintage decor, and warm natural light!

Views of Bearskin neck and peeks of the Harbor from windows

Living Room: Sunlight dances through windows, inviting relaxation in stylish comfort and charm!

Bedroom 1 -Queen Bed

The Waterline

2 bedrooms·1 bath

Rockport • Massachusetts

5(17 reviews)

$949.24 USD total for 3 nights

Oct 31 – Nov 3, 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

Lake Access 4 Bed 3 Bath HOT TUB

HOT TUB TIME!!!

Lake Access 4 Bed 3 Bath HOT TUB

Lake Access 4 Bed 3 Bath HOT TUB

Lake Access 4 Bed 3 Bath HOT TUB

Lake Access 4 Bed 3 Bath HOT TUB

4 bedrooms·3 baths

Billerica • Massachusetts

$2,026.20 USD total for 3 nights

Oct 20 – 23, 2026

Lakeview Getaway with Hot Tub

Lakeview Getaway with Hot Tub

Lakeview Getaway with Hot Tub

Lakeview Getaway with Hot Tub

Lakeview Getaway with Hot Tub

Lakeview Getaway with Hot Tub

3 bedrooms·2 baths

Billerica • Massachusetts

$1,503.09 USD total for 3 nights

Oct 20 – 23, 2026

Balcony Queen+Wisteria Full-Size Beds to 4 guests

Balcony bedroom

Balcony Queen+Wisteria Full-Size Beds to 4 guests

Balcony Queen+Wisteria Full-Size Beds to 4 guests

Balcony Queen+Wisteria Full-Size Beds to 4 guests

Balcony Queen+Wisteria Full-Size Beds to 4 guests

2 bedrooms·1 bath

Shelburne Falls • Massachusetts

5(2 reviews)

$569.50 USD total for 3 nights

Nov 2 – 5, 2026

Charming Loft Kitchen: Enjoy culinary adventures in a sunlit space with rustic beams and modern flair!

The Crow's Nest

The Crow's Nest

The Crow's Nest

The Crow's Nest

The Crow's Nest

1 bedroom·1 bath

Rockport • Massachusetts

5(5 reviews)

$726.58 USD total for 3 nights

Nov 1 – 4, 2026

Your view from the house

Salisbury Sea Breeze Vacation Homes , Ocean Front (On the BEACH)

Fully Equipped Kitchen

Ocean Side - Master BDR (King size bed)

New Master Bathroom

Salisbury Sea Breeze Vacation Home

3 bedrooms·3 baths

Salisbury • Massachusetts

5(2 reviews)

$4,902.45 USD total for 7 nights

May 28 – Jun 4, 2027

Bright and comfortable living room featuring a new queen sleeper sofa, wall-mounted TV, and air conditioning—perfect for relaxing after a beach day or enjoying a cozy evening at your Salisbury Beach getaway.

Welcome to Salisbury Sea Breeze

View of the Kitchen Area

Salisbury Sea Breeze Guest Home

2 bedrooms·1 bath

Salisbury • Massachusetts

5(1 review)

$2,731.31 USD total for 7 nights

Jun 4 – 11, 2027

Perfect Cape Escape ! image 1

Perfect Cape Escape ! image 2

Perfect Cape Escape ! image 3

Perfect Cape Escape ! image 4

Perfect Cape Escape ! image 5

Perfect Cape Escape !

3 bedrooms·2 baths

Harwich • Massachusetts

4.75(8 reviews)

$2,430.00 USD total for 4 nights

Oct 19 – 23, 2026

King size master bed with privacy curtains

King size bed with all comforts

Lofty open space

Open space layout keeps everyone together weather in the kitchen or livingroom

Livingroom featuring a large TV

The Urban Hideout Loft: Sleeps 4 | Private Entrance

0 bedrooms·1 bath

Boston • Massachusetts

$1,593.50 USD total for 3 nights

Oct 25 – 28, 2026