Cuttyhunk

Travel Guide

A coastal landscape with a sandy beach, grassy areas, and a small island with a lighthouse.
A sailboat on calm waters during sunset.
A gazebo in a park with a clear blue sky.
New Bedford Harbor Hotel

New Bedford Harbor Hotel

3 out of 5
222 Union St New Bedford MA
The price is CA $181 per night from Oct 13 to Oct 14
CA $181
CA $202 total
Oct 13 - Oct 14
includes taxes & fees
Stay at this hotel in New Bedford. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. ...
New Bedford Harbor Hotel
Inn on the Square

Inn on the Square

3.5 out of 5
40 North Main Street Falmouth MA
The price is CA $171 per night from Oct 25 to Oct 26
CA $171
CA $232 total
Oct 25 - Oct 26
includes taxes & fees
Stay at this hotel in Falmouth. Enjoy free WiFi, breakfast (surcharge), and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular ...
8.8/10 Excellent! (1,001 reviews)
"Very comfortable bed!"

Reviewed on Oct 10, 2026

Inn on the Square
Vineyard Harbor Motel - Private Beach

Vineyard Harbor Motel - Private Beach

2.5 out of 5
60 Beach Road Vineyard Haven MA
The price is CA $250 per night from Nov 11 to Nov 12
CA $250
CA $279 total
Nov 11 - Nov 12
includes taxes & fees
Book a stay at this beach motel in Vineyard Haven. Enjoy free WiFi, free parking, and a private beach. Our guests praise the helpful staff and the clean rooms ...
Vineyard Harbor Motel - Private Beach
See all 1,227 properties in Cuttyhunk
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Beachside Village Resort

Beachside Village Resort

3 out of 5
45 Surf Drive Falmouth MA
Book a stay at this beach aparthotel in Falmouth. Enjoy free WiFi, an outdoor pool, and daily housekeeping. Our guests praise the property condition in our reviews. ...
9.4/10 Exceptional! (123 reviews)
"It was our anniversary and we asked for a room with a balcony and Ocean view and they got back to us right away, standing that they would set that up for us. The room was perfect. Didn’t realize it had two full bathrooms two balconies overlooking the ocean and it also had the pool with the spa hot ..."

Reviewed on Sep 14, 2026

Beachside Village Resort
Walk to beach, Huge deck off kitchen, roof-deck, king master, close to town

Walk to beach, Huge deck off kitchen, roof-deck, king master, close to town

Middletown RI
Book a stay at this family-friendly vacation home in Middletown. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Cliff Walk and The Breakers ...
10/10 Exceptional! (130 reviews)
"Sara the owner was very accommodating and easy to reach. The home was perfect for 8 women on an annual getaway. Would consider staying here again. It was easy to get in and out of Newport."

Reviewed on Sep 29, 2026

Walk to beach, Huge deck off kitchen, roof-deck, king master, close to town
Quaint, ranch style home in Oak Bluffs with central air

Quaint, ranch style home in Oak Bluffs with central air

Oak Bluffs MA
Stay at this vacation home in Oak Bluffs. Enjoy a garden, balconies, and an in-room coffeemaker. Popular attractions Inkwell Beach and Oak Bluffs Public Library ...
8.4/10 Very good! (5 reviews)
"Would book again"

Reviewed on Jul 27, 2026

Quaint, ranch style home in Oak Bluffs with central air
See all properties in Cuttyhunk
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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