Location

Dates

Guests

Vacation rentals in Chelsea, Massachusetts, United States

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

$77 – $276/ night(excl. fees & taxes)

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

$405.18 USD total for 3 nights

Sep 19 – 22, 2026

Enchanting Hidden Door Escape

4 bedrooms·2 baths

Stoneham • Massachusetts

$1,533.50 USD total for 3 nights

Sep 7 – 10, 2026

Private Beach view

Coastal Charm: Lobster Château

2 bedrooms·2 baths

Swampscott • Massachusetts

$1,190.43 USD total for 3 nights

Sep 7 – 10, 2026

Burlington Mall King Room with Pool & Gym image 1

Burlington Mall King Room with Pool & Gym image 2

Burlington Mall King Room with Pool & Gym image 3

Burlington Mall King Room with Pool & Gym image 4

Burlington Mall King Room with Pool & Gym image 5

Burlington Mall King Room with Pool & Gym

1 bedroom·1 bath

Woburn • Massachusetts

$365.26 USD total for 3 nights

Sep 7 – 10, 2026

Burlington Mall 2 Queen Room with Pool & Gym image 1

Burlington Mall 2 Queen Room with Pool & Gym image 2

Burlington Mall 2 Queen Room with Pool & Gym image 3

Burlington Mall 2 Queen Room with Pool & Gym image 4

Burlington Mall 2 Queen Room with Pool & Gym image 5

Burlington Mall 2 Queen Room with Pool & Gym

1 bedroom·1 bath

Woburn • Massachusetts

$425.58 USD total for 3 nights

Sep 7 – 10, 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)

$732.88 USD total for 3 nights

Sep 8 – 11, 2026

Living room with Open Beam ceiling

The most comfortable chair

Large Smart TV & Wifi

Sea Bird Suite

1 bedroom·1 bath

Marblehead • Massachusetts

4.87(39 reviews)

$732.88 USD total for 3 nights

Sep 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(4 reviews)

$905.59 USD total for 3 nights

Sep 8 – 11, 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

$1,586.77 USD total for 3 nights

Sep 7 – 10, 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

$1,822.88 USD total for 3 nights

Sep 8 – 11, 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)

$2,085.00 USD total for 4 nights

Sep 20 – 24, 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)

$499/ night(excl. fees & taxes)

Carriage House

1 bedroom·1 bath

Sharon • Massachusetts

$400/ night(excl. fees & taxes)

The Spot

1 bedroom·1 bath

Lawrence • Massachusetts

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

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(15 reviews)

$159 – $209/ night(excl. fees & taxes)

our place from the beach

twin beds, back left

House front from yard

Beach Bridge

3 bedrooms·1 bath

Gloucester • Massachusetts

$4,235.00 USD total for 7 nights

Sep 7 – 14, 2026

Anchor's Away @ The Sail Loft!

Living room with dining table

Comfortable chair

View out windows to White Wharf

"Rockport Sail Loft: 2 Bed/1 Bath Oceanfront Haven

2 bedrooms·1 bath

Rockport • Massachusetts

4.87(143 reviews)

$1,160.10 USD total for 3 nights

Sep 7 – 10, 2026

Bedroom 1 -Queen Bed

The Waterline

2 bedrooms·1 bath

Rockport • Massachusetts

$1,143.95 USD total for 3 nights

Oct 31 – Nov 3, 2026

Free cancellation

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)

$892.98 USD total for 3 nights

Sep 7 – 10, 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

$1,000.58 USD total for 3 nights

Nov 3 – 6, 2026

Free cancellation

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(9 reviews)

$975.58 USD total for 3 nights

Oct 17 – 20, 2026

Free cancellation

Living room with Plenty of Sunlight

Bedroom 1 with Queen bed

Open Beam Ceilings- Sail Hooks still in Posts for mending sails!

The Captain's Quarters

2 bedrooms·1 bath

Rockport • Massachusetts

4.82(150 reviews)

$151 – $329/ night(excl. fees & taxes)

Living Room: Timber beams and natural light create a vibrant space for relaxation and fun!

Living Room: Bright and airy space with unique decor, perfect for relaxation and coastal views!

Living Room: Timber beams and a blend of vintage charm invite relaxation and great conversations!

Bedroom: Charming retreat illuminated by natural light with rustic beams and delightful decor!

Bar style eating counter overlooking Bearskin beck

The Captain's Quarters

2 bedrooms·1 bath

Rockport • Massachusetts

5(10 reviews)

$822.36 USD total for 3 nights

Sep 7 – 10, 2026