Location

Dates

Guests

Vacation rentals in Brookline, Massachusetts, United States

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

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

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

Enchanting Hidden Door Escape

4 bedrooms·2 baths

Stoneham • Massachusetts

$1,342.31 USD total for 3 nights

Oct 25 – 28, 2026

Private Beach view

Coastal Charm: Lobster Château

2 bedrooms·2 baths

Swampscott • Massachusetts

$1,446.85 USD total for 3 nights

Oct 26 – 29, 2026

Carriage House

1 bedroom·1 bath

Sharon • Massachusetts

$1,550.00 USD total for 3 nights

Jan 1 – 4, 2027

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

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

Comfortable leather couch and two captains chairs

Barn Doors open to Bedroom

Lots of Sunlight. Great views of beautiful back yard

Eat In Kitchen dining table

Yachtsman Suite

1 bedroom·1 bath

Marblehead • Massachusetts

4.89(35 reviews)

$1,742.33 USD total for 3 nights

Oct 23 – 26, 2026

Living room with Open Beam ceiling

The most comfortable chair

Large Smart TV & Wifi

Sea Bird Suite

1 bedroom·1 bath

Marblehead • Massachusetts

4.88(41 reviews)

$1,512.43 USD total for 3 nights

Oct 23 – 26, 2026

Living room - sectional couch

Bedroom with airconditioner

Well appointed and comfortable

Beams on ceiling

The Sailor's Retreat

1 bedroom·1 bath

Marblehead • Massachusetts

5(5 reviews)

$117 – $748/ night(excl. fees & taxes)

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

Oceanside | Family Friendly Oceanfront Home

Oceanside | Family Friendly Oceanfront Home

Oceanside | Family Friendly Oceanfront Home

Oceanside | Family Friendly Oceanfront Home

Oceanside | Family Friendly Oceanfront Home

Oceanside | Family Friendly Oceanfront Home

4 bedrooms·2 baths

Scituate • Massachusetts

5(104 reviews)

$1,465.00 USD total for 4 nights

Oct 25 – 29, 2026

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

The Egret's Nest

The Egret's Nest

The Egret's Nest

The Egret's Nest

The Egret's Nest

The Egret's Nest

3 bedrooms·2 baths

Marshfield • Massachusetts

$1,019.00 USD total for 7 nights

Oct 20 – 27, 2026