Living room
Bedroom #1
Bedroom #1 Queen bed
Bedroom #2
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)

$954.59 USD total for 3 nights

Oct 24 – 27, 2026

Eating area and sleeping area
Kitchen After 2025 Renovation showing clothes washer-dryer
Back yard from back deck
Frog on 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

$1,307.47 USD total for 3 nights

Oct 19 – 22, 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

$337.45 USD total for 3 nights

Oct 20 – 23, 2026

Bedroom on the second floor with a queen bed
Front view of the home
Forya
Walk to the kitchen
Wide kitchen shot

Queen Bed |Boston|RM 2

1 bedroom·2 baths
Stoneham • Massachusetts

$406.52 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

$298.92 USD total for 3 nights

Nov 1 – 4, 2026

street view
Bedroom
Kitchen
Kitchen
Kitchen

Enchanting Hidden Door Escape

4 bedrooms·2 baths
Stoneham • Massachusetts

$1,512.26 USD total for 3 nights

Oct 19 – 22, 2026

Private Beach view
Living Room
Deck view
Dinning room
Piano

Coastal Charm: Lobster Château

2 bedrooms·2 baths
Swampscott • Massachusetts

$1,424.10 USD total for 3 nights

Oct 26 – 29, 2026

Living Room
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)

$1,887.04 USD total for 3 nights

Oct 23 – 26, 2026

Living room
Living room with Open Beam ceiling
Couch
The most comfortable chair
Large Smart TV & Wifi

Sea Bird Suite

1 bedroom·1 bath
Marblehead • Massachusetts
4.88(41 reviews)

$1,737.66 USD total for 3 nights

Oct 23 – 26, 2026

Living room - sectional couch
Bedroom with airconditioner
Well appointed and comfortable
Living room
Beams on ceiling

The Sailor's Retreat

1 bedroom·1 bath
Marblehead • Massachusetts
5(5 reviews)

$1,096.98 USD total for 3 nights

Oct 19 – 22, 2026

Kitchen
Second Bedroom through door in back of rv
Living room
Master bedroom
Master bath

Turnkey furnished luxury RV getaway

2 bedrooms·1½ baths
Danvers • Massachusetts

$700.00 USD $525.00 USD total for 7 nights

Oct 19 – 26, 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

$1,621.31 USD total for 3 nights

Oct 19 – 22, 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

$2,390.37 USD total for 3 nights

Oct 19 – 22, 2026

King bedroom
Carriage House
Carriage House
Carriage House
Carriage House

Carriage House

1 bedroom·1 bath
Sharon • Massachusetts

$1,550.00 USD total for 3 nights

Jan 1 – 4, 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)

$1,486.00 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 19 – 22, 2026

The Spot
The Spot
The Spot
The Spot
The Spot

The Spot

1 bedroom·1 bath
Lawrence • Massachusetts
$180 – $200/ night(excl. fees & taxes)
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 19 – 26, 2026

Bright, Spacious Bedroom
Bright and spacious room, comfy bed.
Entry Hallway
Private Bath
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

Oct 22 – 25, 2026

Living Room
House
Inside other
House
House

Calder 2

3 bedrooms·1 bath
Gloucester • Massachusetts
Living Room
Beach
House
House
House

Calder 1

2 bedrooms·1 bath
Gloucester • Massachusetts
our place from the beach
full bath
twin beds, back left
Beach Bridge
House front from yard

Beach Bridge

3 bedrooms·1 bath
Gloucester • Massachusetts

$4,235.00 USD total for 7 nights

Oct 19 – 26, 2026