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)

$1,080.91 USD total for 3 nights

Sep 30 – Oct 3, 2026

The Orca Suite
Sunny 1st floor unit with views
Smart TV in living room for streaming
Leather arm chairs
Living room

The Orca

2 bedrooms·1 bath
Rockport • Massachusetts

$1,000.58 USD total for 3 nights

Nov 3 – 6, 2026

The Orca Suite
Sunny 1st floor unit with views
Smart TV in living room for streaming
Leather arm chairs
Living room

The Orca

2 bedrooms·1 bath
Rockport • Massachusetts
5(9 reviews)

$962.41 USD total for 3 nights

Oct 17 – 20, 2026

Living room with Plenty of Sunlight
Living room
Smart TV
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)

$1,076.28 USD total for 3 nights

Nov 1 – 4, 2026

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)

$1,309.54 USD total for 3 nights

Oct 14 – 17, 2026

The Crow's Nest
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
$285/ night(excl. fees & taxes)
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)

$1,106.03 USD total for 3 nights

Oct 14 – 17, 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)

$450.00 USD total for 3 nights

Sep 30 – Oct 3, 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

$2,155.26 USD total for 3 nights

Oct 2 – 5, 2026

Bedroom #1: Oversized room with king sized bed, plenty of reading material, and a white noise machine for a comfortable night’s rest.
Bedroom #1 has a book nook with plenty of reading material for all ages!
Bedroom #2: Another spacious king-sized bed with desk in oversized room.
Fully stocked kitchen with coffee maker, kettle, washer / dryer.
We hope you have sunny weather - but we have umbrellas and a coat tree for wet / snowy days.

Superhost: King Beds! * Kid Friendly. You're Home.

2 bedrooms·1 bath
Boston • Massachusetts
5(216 reviews)

$1,181.55 USD total for 3 nights

Nov 1 – 4, 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

$2,079.32 USD total for 3 nights

Sep 30 – Oct 3, 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

$1,655.89 USD total for 3 nights

Sep 30 – Oct 3, 2026

living and dining area
Back of house
Front entry
livingroom
First floor full bathroom

Boston Historical Urban Oasis

7 bedrooms·3 baths
Boston • Massachusetts

$2,495.09 USD total for 3 nights

Oct 4 – 7, 2026

Bedroom – King Bed & Fantastic City View Seating
Cozy King Bedroom with TV
Cozy King Bedroom with TV
Classy Bedroom Queen Bedroom
Open Living Area

Family Cove: Quiet & Modern 2 bed | Suite 10

2 bedrooms·1 bath
Boston • Massachusetts

$2,274.49 USD total for 3 nights

Oct 18 – 21, 2026

Bedroom – King Bed & Fantastic City View Seating
Cozy King Bedroom with TV
Bedroom 1 – King Bed & TV
Classy Bedroom Queen Bed
Open Living

Sleek Modern 2 Bed: King + Queen | Suite 6

2 bedrooms·1 bath
Boston • Massachusetts

$2,587.62 USD total for 3 nights

Oct 12 – 15, 2026

Bedroom – King Bed
Bedroom – King Bed
Open Living Area
Open Living & Kitchen Area
Living Room – Sofa Bed

Luxury 1BR: Sleek Kitchen + City Charm | Suite 2

1 bedroom·1 bath
Boston • Massachusetts

$2,248.52 USD total for 3 nights

Oct 11 – 14, 2026

Bedroom 1 – King Bed
Bedroom – King Bed & TV
Bedroom – King Bed
Bedroom 2 – Queen Bed
Bedroom – Queen Bed

Trendy 2BR Plus Family Getaway | Suite 4

2 bedrooms·1 bath
Boston • Massachusetts

$3,628.24 USD total for 3 nights

Oct 25 – 28, 2026

Cozy King Bedroom
Amazing city views from the large bay windows in the sitting area
Cozy King Bedroom with City View
Modern Comfort Living Area – Pull Out Seating
Modern Comfort Living Area – TV & Pull Out Seating

Elegant 1BR Plus: Sky-High City Views + King | Suite 9

2 bedrooms·1 bath
Boston • Massachusetts

$2,661.47 USD total for 3 nights

Oct 30 – Nov 2, 2026

Bedroom – King Bed & Fantastic City View Seating
Cozy King Bedroom with TV
Cozy King Bedroom with TV
Classy Queen Bedroom
Open Living Area

Modern Luxury 2BR | King + Queen | Suite 8

2 bedrooms·1 bath
Boston • Massachusetts

$3,352.03 USD total for 3 nights

Oct 27 – 30, 2026

Cozy King Bedroom
Cozy King Bedroom
Enjoy the view from the large bay windows in the sitting area
Relaxing Den Area with Pull Out Seating
Relaxing Den Area – TV & Pull Out Seating

Elegant 1BR Plus: Cityscape Views + King and pull out Queen| Suite 5

2 bedrooms·1 bath
Boston • Massachusetts

$3,280.92 USD total for 3 nights

Oct 29 – Nov 1, 2026

Cozy King Bedroom
Fantastic City View Seating from the large bay windows
Cozy King Bedroom with City View
Relaxing Den Area with Pull Out Seating
Relaxing Den Area – TV & Pull Out Seating

Cityscape 1BR Plus: King + Queen Pull-out | Suite 7

2 bedrooms·1 bath
Boston • Massachusetts

$2,892.57 USD total for 3 nights

Oct 26 – 29, 2026

City View Bedroom – King Bed
Fantastic City View Seating
Bedroom – King Bed
Living Area – TV & Seating
Open Living Area

Front Row City Views: 1BR Suite with King Bed | Suite 3

1 bedroom·1 bath
Boston • Massachusetts

$1,328.24 USD total for 3 nights

Nov 7 – 10, 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

$1,820.51 USD total for 3 nights

Oct 18 – 21, 2026

Living Room
New flooring (2022)
Living Room
Living Room
Vaulted Ceiling

Oceanfront Penthouse Salisbury

5 bedrooms·2 baths
Salisbury • Massachusetts
5(182 reviews)

$1,635.00 USD total for 3 nights

Oct 5 – 8, 2026