Title: Cuttyhunk Vacation Rentals from CA $238: Short-Term Rentals for 2025 | Expedia.ca [Cuttyhunk Travel Guide](https://expedia.ca/Cuttyhunk.dx3000441000)[Hotels in Cuttyhunk](https://expedia.ca/Cuttyhunk-Hotels.d3000441000.Travel-Guide-Hotels)[Flights to Cuttyhunk](https://expedia.ca/Cheap-Flights-To-Cuttyhunk.d3000441000.Travel-Guide-Flights)[Cuttyhunk Car Rentals](https://expedia.ca/Car-Rentals-In-Cuttyhunk.d3000441000.Car-Rental-Guide)[Cuttyhunk Vacation Packages](https://expedia.ca/Cuttyhunk.d3000441000.Destination-Travel-Guides) ![Default HTG hotel image](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_lodging_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Cuttyhunk Vacation Rentals ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) ![bed illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check prices for these dates In two weeks [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=3000441000&startDate=2025-10-17&endDate=2025-10-19&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=3000441000&startDate=2025-10-31&endDate=2025-11-02&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=3000441000&startDate=2025-11-28&endDate=2025-11-30&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=3000441000&startDate=2025-12-26&endDate=2025-12-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Vacation Rentals in Cuttyhunk ![On the beach, white sand](https://images.trvl-media.com/lodging/2000000/1160000/1154100/1154022/7f1dbbf7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, coffee/tea maker, cookware/dishes/utensils](https://images.trvl-media.com/lodging/2000000/1160000/1154100/1154022/910c8a68.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/2000000/1160000/1154100/1154022/65350001.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![BBQ/picnic area](https://images.trvl-media.com/lodging/2000000/1160000/1154100/1154022/a3da66ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### InnSeason Resorts Captain's Quarters Falmouth Heights 9.8/10 Exceptional (181) "Great location and helpful staff" [](https://www.expedia.ca/Falmouth-Hotels-InnSeason-Resorts-Captains-Quarters.h1154022.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/70000000/69240000/69239700/69239615/9c91c77e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, internet](https://images.trvl-media.com/lodging/70000000/69240000/69239700/69239615/1ef031e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/70000000/69240000/69239700/69239615/afa6faf6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/70000000/69240000/69239700/69239615/a80877bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Dog Friendly Cottages w/ easy access to Newport, beaches, trails and vineyards Middletown 9.8/10 Exceptional (157) "Great place, loved it! Had everything we needed." CA $194 CA $249 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Newport-Hotels-Dog-Friendly-Cottages-W-Easy-Access-To-Newport.h69239615.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/23000000/22140000/22130600/22130502/ce6e4469.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach](https://images.trvl-media.com/lodging/23000000/22140000/22130600/22130502/7c4a0470.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/23000000/22140000/22130600/22130502/e77f579c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/23000000/22140000/22130600/22130502/057c470c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs Oak Bluffs 6.4/10 (31) "The weather was perfect and our crew made the best of our trip." [](https://www.expedia.ca/Oak-Bluffs-Hotels-Tranquil.h22130502.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/2000000/1160000/1154100/1154021/94ed0eee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Studio, 1 Queen Bed with Sofa bed | Private kitchen](https://images.trvl-media.com/lodging/2000000/1160000/1154100/1154021/dcdcbc09.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Studio, 1 Queen Bed with Sofa bed | Private kitchen](https://images.trvl-media.com/lodging/2000000/1160000/1154100/1154021/198567b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach](https://images.trvl-media.com/lodging/2000000/1160000/1154100/1154021/w1200h800x0y0-42e49c7c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beachside Village Resort Falmouth 9.2/10 Wonderful (99) "Great location! Nice property! " [](https://www.expedia.ca/Falmouth-Hotels-Beachside-Village-Resort-By-VRI-Americas.h1154021.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/49000000/48490000/48483300/48483278/acf9512c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/49000000/48490000/48483300/48483278/01b70ed1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/49000000/48490000/48483300/48483278/b5bfe5f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/49000000/48490000/48483300/48483278/1925ab75.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### MOST CHIC SPOT! Your Martha's Vineyard Getaway! Oak Bluffs 10/10 Exceptional (7) "Our kids and their friends had so much fun in the beautifully finished basement. Easy access to beach and ferry, would love to go back every year, the host was wonderful." CA $767 CA $1,691 total includes taxes & fees Oct 6 - Oct 7 [](https://www.expedia.ca/Oak-Bluffs-Hotels-MOST-CHIC-SPOT-Your-Marthas-Vineyard-Getaway.h48483278.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/50000000/49040000/49037700/49037659/94064cd7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/50000000/49040000/49037700/49037659/9c73882b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/50000000/49040000/49037700/49037659/e8b4c248.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/50000000/49040000/49037700/49037659/f65d6d1e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Downtown Captain's Mansion- The Dexter- Family, pet, and event friendly Tisbury 10/10 Exceptional (64) "The house was well stocked and had everything you could need. " [](https://www.expedia.ca/Vineyard-Haven-Hotels-Downtown-Captains-House.h49037659.Hotel-Information) ![Beach](https://images.trvl-media.com/lodging/36000000/35390000/35381500/35381442/11aa19af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/36000000/35390000/35381500/35381442/8770ae26.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/36000000/35390000/35381500/35381442/7f8278de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/36000000/35390000/35381500/35381442/2743c156.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy getaway in a central location w/ a full kitchen & furnished deck Oak Bluffs 6.8/10 (23) "The furniture and amenities provided were good" [](https://www.expedia.ca/Oak-Bluffs-Hotels-Cozy-Getaway-In-A-Central-Location-W-A-Full-Kitchen-Furnished-Deck.h35381442.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/107000000/106160000/106156300/106156274/63bfffde.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave](https://images.trvl-media.com/lodging/107000000/106160000/106156300/106156274/30b1c10b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/107000000/106160000/106156300/106156274/210d8571.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/107000000/106160000/106156300/106156274/1dbbb0ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Renovated One Bedroom Apartment Downtown Falmouth Minutes From the Beach Falmouth 10/10 Exceptional (1) "The location was great and the pullouts were comfortable. The only downside is the walk through bathroom." [](https://www.expedia.ca/Falmouth-Hotels-Renovated-One-Bedroom-Apartment-Downtown-Falmouth-Minutes-From-The-Beach.h106156274.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/34000000/33570000/33568700/33568664/270-9046fa20.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/34000000/33570000/33568700/33568664/270-27e28fd2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/34000000/33570000/33568700/33568664/d5a5e801.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, DVD player, books](https://images.trvl-media.com/lodging/34000000/33570000/33568700/33568664/57151c46.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### By the Water - Steps to the Beach - 4Br, AC, Views of Vineyard Sound Falmouth 9.8/10 Exceptional (23) "We had a great week staying at this property. It's well maintained and had plenty of room for a family getaway to the Cape. Steps away from the beach, this property is well taken care of and had everything we needed for a comfortable stay. This would be our first choice for any future trips to the Cape." [](https://www.expedia.ca/Falmouth-Hotels-By-The-Water-Steps-To-The-Beach-4Br.h33568664.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/34000000/33570000/33565200/33565185/5a314b62.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/34000000/33570000/33565200/33565185/6fee03bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/34000000/33570000/33565200/33565185/fcc15c5f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/34000000/33570000/33565200/33565185/a53c3816.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quiet 2-Bed, 2-Bath Condo with Spacious Sundeck & Tennis Courts Edgartown 9.8/10 Exceptional (80) "Central property with all essentials!" [](https://www.expedia.ca/Oak-Bluffs-Hotels-Quiet-2-Bed.h33565185.Hotel-Information) ![Beach nearby](https://images.trvl-media.com/lodging/113000000/112450000/112447700/112447645/a2ad4532.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/113000000/112450000/112447700/112447645/1b6c0e4f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/113000000/112450000/112447700/112447645/faa2d194.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/113000000/112450000/112447700/112447645/2ff350d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ground-Floor Studio w/ 2 King Beds & Kitchenette (103) Falmouth Heights 6.0/10 (2) "Our trip was a last minute decision, and needed to stay just one night. The location, the fast response, clear instructions, cleanliness, assigned parking and pricing all came together very nicely! " CA $189 CA $238 total includes taxes & fees Oct 6 - Oct 7 [](https://www.expedia.ca/Falmouth-Hotels-First-Floor-Walkout-Suite-With-Ocean-Views.h112447645.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/33000000/32510000/32506700/32506609/67f1fd01.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/33000000/32510000/32506700/32506609/dbbc4329.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/33000000/32510000/32506700/32506609/e022d41b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/33000000/32510000/32506700/32506609/e811309b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Recent Construction, Fire Pit, Kayaks, Close to Town, and Beach. Easton’s Point. Middletown 10/10 Exceptional (103) "Very enjoyable " [](https://www.expedia.ca/Newport-Hotels-New-Construction.h32506609.Hotel-Information) ![TV, DVD player, books](https://images.trvl-media.com/lodging/117000000/116540000/116536200/116536158/42c94b4e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116540000/116536200/116536158/18c0ec5f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/117000000/116540000/116536200/116536158/f1f5545c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, internet, bed sheets](https://images.trvl-media.com/lodging/117000000/116540000/116536200/116536158/803a09fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Spacious colonial home close to town with AC, porches, & W/D Oak Bluffs 10/10 Exceptional (5) [](https://www.expedia.ca/Oak-Bluffs-Hotels-Spacious-Colonial-Home-Close-To-Town-With-AC.h116536158.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/77000000/76260000/76252500/76252485/2a366c1e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/77000000/76260000/76252500/76252485/b8b9588b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/77000000/76260000/76252500/76252485/ad84f765.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/77000000/76260000/76252500/76252485/df408bfb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Uniquely designed island retreat with fast WiFi & private W/D - dogs welcome West Tisbury 8.8/10 Excellent (33) "The peaceful woodland setting is just beautiful! Enjoyed a quiet stay in this spacious one bedroom house. The porch wraps around entire house and gave our morning coffee and breakfast a very special vacation feel." [](https://www.expedia.ca/Vineyard-Haven-Hotels-Uniquely-Designed-Island-Retreat-With-Fast-WiFi-Private-WD-Dogs-Welcome.h76252485.Hotel-Information) ![On the beach](https://images.trvl-media.com/lodging/36000000/35250000/35249400/35249336/9cffd5ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/36000000/35250000/35249400/35249336/ea5bb211.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/36000000/35250000/35249400/35249336/fc4cf300.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/36000000/35250000/35249400/35249336/d8143125.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Perfect For Wedding Guest, Friends Getaway Or Family Vacation Middletown 10/10 Exceptional (9) "Clean property and great location. Owners were very accommodating. Right across from beach and short ride to downtown Newport." [](https://www.expedia.ca/Middletown-Hotels-Perfect-For-Wedding-Guest.h35249336.Hotel-Information) ![TV, fireplace, books](https://images.trvl-media.com/lodging/49000000/48490000/48483300/48483217/31f34cb5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, books](https://images.trvl-media.com/lodging/49000000/48490000/48483300/48483217/f9457118.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, books](https://images.trvl-media.com/lodging/49000000/48490000/48483300/48483217/8ca80e40.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/49000000/48490000/48483300/48483217/e6152028.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### A NOSTALGIC SPACE! Your Martha's Vineyard Getaway! Oak Bluffs 9.0/10 Wonderful (2) "The house was lovely. Very clean and orderly. Beautiful back porch that we enjoyed very much. The beds were very comfortable. Our only complaint was the Master bathroom needs some updating. The shower head desperately needs to be changed and the lighting is extremely poor. Also, only 1 half size mirror on the whole first floor. Other than that, it was perfect." CA $244 CA $935 total includes taxes & fees Oct 6 - Oct 7 [](https://www.expedia.ca/Oak-Bluffs-Hotels-A-NOSTALGIC-SPACE-Your-Marthas-Vineyard-Getaway.h48483217.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33650000/33644400/33644369/bb406a43.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, video games, Netflix](https://images.trvl-media.com/lodging/34000000/33650000/33644400/33644369/dde7e9ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/34000000/33650000/33644400/33644369/a4dd4f13.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/34000000/33650000/33644400/33644369/7d765850.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Modern, luxury 5-bed, 4.5-bath w/full basement! Now booking for 2026! Oak Bluffs 10/10 Exceptional (71) "Large home with plenty of room for extended family. Located in quiet neighborhood close to Oak Bluffs, would highly recommend." [](https://www.expedia.ca/Oak-Bluffs-Hotels-Modern.h33644369.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/115000000/114220000/114210100/114210026/ed35bf2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/115000000/114220000/114210100/114210026/61971813.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/115000000/114220000/114210100/114210026/5714b8e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/115000000/114220000/114210100/114210026/dfb1aaf7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming newly renovated home in Little Compton. Little Compton 10/10 Exceptional (5) [](https://www.expedia.ca/Little-Compton-Hotels-Charming-Newly-Renovated-Home-In-Little-Compton.h114210026.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/108000000/107810000/107802400/107802346/80f792bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/108000000/107810000/107802400/107802346/4e918ad1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/108000000/107810000/107802400/107802346/e0118af9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![5 bedrooms, iron/ironing board, internet, bed sheets](https://images.trvl-media.com/lodging/108000000/107810000/107802400/107802346/4bdce25c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Spacious home in central location with beautiful patio, pool table, W/D, & AC Oak Bluffs 10/10 Exceptional (4) "Absolutely loved our stay at this Oak Bluffs home! The location was perfect—just a 20-minute walk to downtown—and the house itself was warm, inviting, and beautifully laid out with an open-air feel. The kitchen was fully stocked, the beds were super comfortable, and the outdoor shower was a wonderful bonus. We felt completely relaxed and free during our stay. Can’t wait to come back next summer!" [](https://www.expedia.ca/Oak-Bluffs-Hotels-Spacious-Home-In-Central-Location-With-Beautiful-Patio.h107802346.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/97000000/96450000/96443900/96443890/323dea9c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/97000000/96450000/96443900/96443890/36ee50ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, in-room safe, desk, WiFi](https://images.trvl-media.com/lodging/97000000/96450000/96443900/96443890/270-a8265849.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/97000000/96450000/96443900/96443890/d5dacd66.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Retreat to Martha's Vineyard with a Private Pool & Outdoor Living in Oak Bluffs Oak Bluffs 10/10 Exceptional (7) "Clean, functional, lots of space " [](https://www.expedia.ca/Oak-Bluffs-Hotels-Retreat-To-Marthas-Vineyard-With-A-Private-Pool-Outdoor-Living-In-Oak-Bluffs.h96443890.Hotel-Information) 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. [View all properties](https://expedia.ca/Hotel-Search?startDate=2025-10-19&endDate=2025-10-20®ionId=3000441000&adults=2&sort=RECOMMENDED&openPlayBack=true) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FCuttyhunk-Vacation-Rentals.d3000441000.Travel-Guide-VacationRentals)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FCuttyhunk-Vacation-Rentals.d3000441000.Travel-Guide-VacationRentals) ## Top Cuttyhunk Hotel Reviews ![New Bedford Harbor Hotel, an Ascend Collection Hotel](//images.trvl-media.com/lodging/24000000/23260000/23251300/23251279/9aa17686_y.jpg) ### New Bedford Harbor Hotel, an Ascend Collection Hotel 10/10 Excellent "." [](https://expedia.ca/New-Bedford-Hotels-New-Bedford-Harbor-Hotel.h23251279.Hotel-Information) ![The East Island Reserve Hotel](//images.trvl-media.com/lodging/18000000/17450000/17443700/17443695/ebabd3a5_y.jpg) ### The East Island Reserve Hotel 10/10 Excellent "Very clean and quiet. No contact with staff." [](https://expedia.ca/Newport-Hotels-The-East-Island-Reserve-Hotel.h17443695.Hotel-Information) ![Falmouth Tides ](//images.trvl-media.com/lodging/70000000/69380000/69374600/69374512/3742adf6_y.jpg) ### Falmouth Tides 10/10 Excellent "We were very " [](https://expedia.ca/Falmouth-Hotels-Falmouth-Tides-Motel.h69374512.Hotel-Information) ![Iris Hotel Cape Cod ](//images.trvl-media.com/lodging/1000000/20000/12000/11989/63513190_y.jpg) ### Iris Hotel Cape Cod 10/10 Excellent "Floor needs cleaning" [](https://expedia.ca/Falmouth-Hotels-Hotel-Cape-Cod.h11989.Hotel-Information) ![Falmouth Inn](//images.trvl-media.com/lodging/1000000/900000/893200/893142/a26689a2_y.jpg) ### Falmouth Inn 10/10 Excellent "We attened an event very close ny at a marina. We were able to park and walk. Hotel has a restaurant and bar, but lots of options withinn walking distsnce. Close to main street shopping with lots of shops and restaurants. Not a big deal, but we arrivrd at 1pm, check in is at 3pm. Our room was ready but they said $20 extra to check in early, we just left our truck and went out and came back later for our keys. Room was clean. Bed was comfortable. Its a basic hotel, we would stay again " [](https://expedia.ca/Falmouth-Hotels-Falmouth-Inn.h893142.Hotel-Information) ![Seaport Resort & Marina](//images.trvl-media.com/lodging/1000000/550000/544000/543980/b06f5566_y.jpg) ### Seaport Resort & Marina 10/10 Excellent "Yes AC fine" [](https://expedia.ca/Fairhaven-Hotels-Seaport-Inn-Marina.h543980.Hotel-Information) ![Atlantic Beach Hotel Newport](//images.trvl-media.com/lodging/1000000/330000/327200/327192/f0b3ff3f_y.jpg) ### Atlantic Beach Hotel Newport 10/10 Excellent "Perfect location very pleased with service at the hotel" [](https://expedia.ca/Newport-Hotels-Atlantic-Beach-Hotel-Newport.h327192.Hotel-Information) ![Wyndham Newport Hotel](//images.trvl-media.com/lodging/2000000/1110000/1101800/1101766/43f10503_y.jpg) ### Wyndham Newport Hotel 10/10 Excellent "Great place. Close to everything " [](https://expedia.ca/Newport-Hotels-Wyndham-Newport-Hotel.h1101766.Hotel-Information) ![Vineyard Harbor Motel - Private Beach](//images.trvl-media.com/lodging/61000000/60390000/60384600/60384563/6bd7fc20_y.jpg) ### Vineyard Harbor Motel - Private Beach 10/10 Excellent "Rooms were clean and comfortable a quick walk to the center of town PLUS there was a cute little beach!" [](https://expedia.ca/Vineyard-Haven-Hotels-Vineyard-Harbor-Motel.h60384563.Hotel-Information) ## Find out more about Cuttyhunk **Everything you need to know about** **Cuttyhunk** **vacation rentals** Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Cuttyhunk vacation rental for you. At Expedia, you can take your pick from [private vacation homes](https://www.expedia.ca/aa/PrivateVacationHomes), [apartments](https://www.expedia.ca/aa/Apartments), cottages, [cabins](https://www.expedia.ca/aa/Cabins), villas... The list goes on, and on… and on! There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Cuttyhunk vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.  **Cuttyhunk vacation rentals: An excellent choice for every season** Whenever you want to travel, a warm welcome awaits you in Cuttyhunk. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in .  Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Cuttyhunk vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Cuttyhunk vacation rentals we have selected for you start as low as CA $238 per night. Entering your travel dates in the search wizard you might find even better deals! **How to find incredible deals on Cuttyhunk rentals** At Expedia, we put the best Cuttyhunk vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.  To find some top Cuttyhunk rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Cuttyhunk vacation. If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Cuttyhunk. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.  ## Explore a world of travel with Expedia - Trending destinations on Expedia.ca - All accommodation types in Cuttyhunk ### Trending destinations on Expedia.ca - [Canmore Vacation Rentals](https://www.expedia.ca/Canmore-Vacation-Rentals.d10131.Travel-Guide-VacationRentals) - [Maui Vacation Rentals](https://www.expedia.ca/Maui-Vacation-Rentals.d180073.Travel-Guide-VacationRentals) - [Kelowna Vacation Rentals](https://www.expedia.ca/Kelowna-Vacation-Rentals.d3997.Travel-Guide-VacationRentals) - [Whistler Vacation Rentals](https://www.expedia.ca/Whistler-Vacation-Rentals.d4115.Travel-Guide-VacationRentals) - [Florida Vacation Rentals](https://www.expedia.ca/Destinations-In-Florida.d211.Vacation-Rental-Destinations) - [Victoria Vacation Rentals](https://www.expedia.ca/Victoria-Vacation-Rentals.d4138.Travel-Guide-VacationRentals) - [Vancouver Vacation Rentals](https://www.expedia.ca/Vancouver-Vacation-Rentals.d178315.Travel-Guide-VacationRentals) - 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[Guest Houses in Cuttyhunk](https://expedia.ca/Cuttyhunk-Guest-Houses.d3000441000-aaGuestHouses.Travel-Guide-Accommodation) - [Holiday Park Resorts in Cuttyhunk](https://expedia.ca/Cuttyhunk-Holiday-Parks.d3000441000-aaHolidayParks.Travel-Guide-Accommodation) - [Inns in Cuttyhunk](https://expedia.ca/Cuttyhunk-Inns.d3000441000-aaInns.Travel-Guide-Accommodation) ### Expedia's Latest Trends Hotels - [Hampton Inn & Suites Grand Forks](https://expedia.ca/Grand-Forks-Hotels-Hampton-Inn-Suites-Grand-Forks.h6190356.Hotel-Information) - [Best Hotels in Brighton](https://expedia.ca/Brighton-Hotels.d180785.Travel-Guide-Hotels) - [Banff National Park hotels](https://expedia.ca/Banff-National-Park-Hotels.0-l602291-0.Travel-Guide-Filter-Hotels) - [Lake Louise All Inclusive Resorts and Hotels](https://expedia.ca/Lake-Louise-Hotels-All-Inclusive-Hotel.0-0-d10115-tAllInclusiveHotel.Travel-Guide-Filter-Hotels) - [Regina Hotels with Free Breakfast](https://expedia.ca/Regina-Hotels-Hotels-With-Free-Breakfast.0-0-d4053-tHotelswithFreeBreakfast.Travel-Guide-Filter-Hotels) - 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Scan the QR code with your device camera and download our app ![QR code to download the app](data:image/png;base64,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)