Vacation Homes in Cuttyhunk, MA
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Top Vacation Homes in Cuttyhunk

Cozy getaway in a central location w/ a full kitchen & furnished deck

DISCOUNT WEEK OF JULY 19-26!! Ocean views, Walk to Beach, Central AC, 4 Car Pk

☼ Westport Point ☼ beach house on 1/2 acre easy access to beach/historic village

Modern, luxury 5-bed, 4.5-bath w/full basement! Now booking for 2026!

Uniquely designed island retreat with fast WiFi & private W/D - dogs welcome

Walk to beach! Great large outdoor patio. Still booking fall 2025!

Recent Construction, Fire Pit, Kayaks, Close to Town, and Beach. Easton’s Point.

Charming cottage with deck, yard, & AC - walk to beach, Main Street, & ferry

Surfside! Fantastic Beach House, Near Restaurants, Cliff Walk, Close to Downtown

Luxury Loft Historic Center Oak Bluffs

Best Kept Secret Retreat for Adults with Water & Golf Course Views!
Top hotels in Cuttyhunk

Wyndham Newport Hotel
Find the Best Vacation Homes in Cuttyhunk
Why book a vacation home in Cuttyhunk?
Vacation homes in Cuttyhunk make for a different travel experience. Your holiday home will allow you to feel at home during your visit. You’ll usually have more space, more privacy, and extra amenities not typically included with hotel stays.
How much is a vacation home in Cuttyhunk?
Private Cuttyhunk rental homes range between $123 - $419 per night. Prices change based on seasonal demand, travel dates, property location, capacity, amenities, etc.
What are the cancellation and flexibility options on Travelocity?
To cancel your vacation home, you must reach out to the individual property manager. Their contact details are available in your itinerary. For more information, head over to our customer service portal. Use the ‘free cancellation’ or ‘reserve now, pay later’ filters to find the most flexible options for your bookings.
What amenities should I look out for in a vacation home?
There are some exciting amenities available in Cuttyhunk vacation home rentals. You might look for Cuttyhunk rental houses with a private pool or free Wi-Fi. Some popular amenities also include a private hot tub, air-conditioning, laundry facilities, and a games room.
Vacation rentals in Cuttyhunk offer other accommodations that may interest you. Some have resort-like amenities such as a fitness center, bar/lounge, or swimming pool.
When is the best time to rent a vacation home in Cuttyhunk?
You’ll typically get cheaper rates when staying during the off-season, . Prices are usually at their lowest for stays in . are the most popular months to visit.
Why book a vacation home with Travelocity?
Travel smart with Travelocity. Search over 1 million properties worldwide and access an incredible selection of holiday homes in Cuttyhunk. Our members save 10% or more on select hotels, and if you find a lower price, we’ll match it with our Price Match Guarantee. Get started finding Cuttyhunk hotels and vacation homes that best suit your stay. We also have deals for flights, and Cuttyhunk car rentals. You’ll save even more when you bundle your items into a Cuttyhunk vacation package!
How many vacation homes are available to book in Cuttyhunk?
There are 557 rental homes in Cuttyhunk. Enter your travel dates to check availability.
How do I find the best price for a vacation home in Cuttyhunk?
Private vacation homes vary in price, and we’ll help you get the best deal possible. Use the map feature to compare rental house prices in different neighborhoods. Also, try adjusting your dates to compare nightly rates within a similar timeframe.
Cuttyhunk Vacation Homes essential information
Accommodation | 557 Vacation Homes |
---|---|
Lowest Price | $123 |
Highest Price | $419 |
Popular accommodation | Cozy getaway in a central location w/ a full kitchen & furnished deck, DISCOUNT WEEK OF JULY 19-26!! Ocean views, Walk to Beach, Central AC, 4 Car Pk, ☼ Westport Point ☼ beach house on 1/2 acre easy access to beach/historic village, Modern, luxury 5-bed, 4.5-bath w/full basement! Now booking for 2026!, Uniquely designed island retreat with fast WiFi & private W/D - dogs welcome, Walk to beach! Great large outdoor patio. Still booking fall 2025!, Recent Construction, Fire Pit, Kayaks, Close to Town, and Beach. Easton’s Point., Charming cottage with deck, yard, & AC - walk to beach, Main Street, & ferry, Surfside! Fantastic Beach House, Near Restaurants, Cliff Walk, Close to Downtown, Luxury Loft Historic Center Oak Bluffs, Best Kept Secret Retreat for Adults with Water & Golf Course Views!, Stunning Luxury House with Sunset and Private Beach |
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