Location

Dates

Guests

Vacation rentals in Winthrop, Massachusetts, United States

Bar table and Stool

Luxurious House-Harvard/PorterT 5BR/4Bath, Parking

5 bedrooms·4 baths

Somerville • Massachusetts

4.9(301 reviews)

$4,338.75 USD $3,919.88 USD total for 5 nights

Nov 13 – 18, 2026

living and dining area

First floor full bathroom

Boston Historical Urban Oasis

7 bedrooms·3 baths

Boston • Massachusetts

$2,180.98 USD total for 3 nights

Nov 9 – 12, 2026

Bedroom #1 Queen bed

Bedroom #2 with queen bed and crib

Boston's Jamaica Plain w/ parking, A/C, laundry

2 bedrooms·1 bath

Boston • Massachusetts

4.81(120 reviews)

$876.75 USD total for 3 nights

Nov 9 – 12, 2026

3BR Retreat · Sleeps 8 · Coolidge Corner T image 1

3BR Retreat · Sleeps 8 · Coolidge Corner T image 3

3BR Retreat · Sleeps 8 · Coolidge Corner T image 4

3BR Retreat · Sleeps 8 · Coolidge Corner T image 5

3BR Retreat · Sleeps 8 · Coolidge Corner T image 6

3BR Retreat · Sleeps 8 · Coolidge Corner T

3 bedrooms·1 bath

Brookline • Massachusetts

4.5(2 reviews)

$1,107.00 USD total for 3 nights

Nov 9 – 12, 2026

Private Beach view

Coastal Charm: Lobster Château

2 bedrooms·2 baths

Swampscott • Massachusetts

$1,216.22 USD total for 3 nights

Nov 14 – 17, 2026

Eating area and sleeping area

Kitchen After 2025 Renovation showing clothes washer-dryer

Back yard from back deck

House From Street

Cambridge Studio Apartment

1 bedroom·1 bath

Cambridge • Massachusetts

4.67(400 reviews)

$150/ night(excl. fees & taxes)

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

$1,137.70 USD total for 3 nights

Nov 5 – 8, 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

$314.86 USD total for 3 nights

Nov 5 – 8, 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

$314.86 USD total for 3 nights

Nov 5 – 8, 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

$344.09 USD total for 3 nights

Nov 5 – 8, 2026

Enchanting Hidden Door Escape

4 bedrooms·2 baths

Stoneham • Massachusetts

$1,437.91 USD total for 3 nights

Nov 5 – 8, 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(36 reviews)

$767.89 USD total for 3 nights

Nov 12 – 15, 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)

$755.05 USD total for 3 nights

Nov 8 – 11, 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)

$626.68 USD total for 3 nights

Feb 28 – Mar 3, 2027

Second Bedroom through door in back of rv

Turnkey furnished luxury RV getaway in New England

2 bedrooms·1½ baths

Danvers • Massachusetts

$4,500.00 USD $2,250.00 USD total for 90 nights

Apr 1 – Jun 30, 2027

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)

$1,435.00 USD total for 4 nights

Nov 14 – 18, 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

Nov 5 – 8, 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

$1,468.55 USD total for 3 nights

Nov 5 – 8, 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

$1,713.63 USD total for 3 nights

Nov 8 – 11, 2026

Carriage House

1 bedroom·1 bath

Sharon • Massachusetts

$1,550.00 USD total for 3 nights

Jan 1 – 4, 2027

Bright, Spacious Bedroom

Bright and spacious room, comfy bed.

Cape Ann sunset (up the road at Plum Cove)

Quirky, Bright, Spacious Private Room Near Water

1 bedroom·1 bath

Gloucester • Massachusetts

5(17 reviews)

$552.00 USD total for 3 nights

Nov 12 – 15, 2026

Calder 2

3 bedrooms·1 bath

Gloucester • Massachusetts

Calder 1

2 bedrooms·1 bath

Gloucester • Massachusetts

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

Nov 5 – 12, 2026