Title: Cuttyhunk Vacation Home Rentals : Search Top Private Vacation Homes for Rent | Expedia.ca [Cuttyhunk Travel Guide](https://expedia.ca/Cuttyhunk.dx3000441000)[Hotels in Cuttyhunk](https://expedia.ca/Cuttyhunk-Hotels.d3000441000.Travel-Guide-Hotels)[Vacation Rentals in Cuttyhunk](https://expedia.ca/Cuttyhunk-Vacation-Rentals.d3000441000.Travel-Guide-VacationRentals)[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://media.expedia.com/media/content/shared/images/travelguides/sem-hotels-tablet.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Cuttyhunk Vacation Rentals ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![](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) ![](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 Next weekend [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=3000441000&startDate=2025-10-31&endDate=2025-11-02&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=3000441000&startDate=2025-11-07&endDate=2025-11-09&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=3000441000&startDate=2025-11-21&endDate=2025-11-23&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=3000441000&startDate=2025-12-19&endDate=2025-12-21&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Cuttyhunk Vacation Homes ![On the beach, sun loungers, beach towels](https://images.trvl-media.com/lodging/103000000/102910000/102903600/102903531/w1170h1108x0y0-1f9b0efc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/103000000/102910000/102903600/102903531/w1170h1522x0y0-c83022a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/103000000/102910000/102903600/102903531/43c8d00c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/103000000/102910000/102903600/102903531/ac544bb6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quaint 1 Bed 1 bath private beach home. Long term renters welcome for winter! Dartmouth 10/10 Exceptional (17) "Home was excellent. Well appointed and everything to make my stay comfortable. Thanks to the hosts and hope to stay again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Frank B. CA $189 CA $491 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/South-Dartmouth-Hotels-Quaint-1-Bed-1-Bath-Private-Beach-Home-Family-Friendly-Sleeps-4-Guests.h102903531.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33570000/33564900/33564802/f9259183.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/34000000/33570000/33564900/33564802/32ea6769.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/34000000/33570000/33564900/33564802/dc424ea5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/34000000/33570000/33564900/33564802/7d2038e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Located Steps Away To Main Street And .7 Miles From Surf Drive Beach Falmouth 10/10 Exceptional (203) "Loved this spot. So easy to get to downtown and Surf Beach. It was fabulous and clean!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anne S. CA $147 CA $594 total includes taxes & fees Oct 28 - Oct 29 [](https://www.expedia.ca/Falmouth-Hotels-Located-Steps-Away-To-Main-Street-And-7-Miles-From-Surf-Drive-Beach.h33564802.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/49000000/48490000/48483300/48483217/8ca80e40.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) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/49000000/48490000/48483300/48483217/60505837.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." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Leon R. CA $245 CA $931 total includes taxes & fees Oct 25 - Oct 26 [](https://www.expedia.ca/Oak-Bluffs-Hotels-A-NOSTALGIC-SPACE-Your-Marthas-Vineyard-Getaway.h48483217.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/93000000/92440000/92431600/92431523/31b29a06.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/93000000/92440000/92431600/92431523/9054a4ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/93000000/92440000/92431600/92431523/929c0e22.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/93000000/92440000/92431600/92431523/7c82f0d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ellery Bungalow #51- Island Calm Near Newport Middletown 9.6/10 Exceptional (94) "My family had an amazing stay at this bungalow. It is very clean and offered everything we needed for our stay in Newport. The beach is very close and there are plenty of restaurants and convenience store within walking distance. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tamara C. CA $151 CA $615 total includes taxes & fees Nov 17 - Nov 18 [](https://www.expedia.ca/Middletown-Hotels-Ellery-Bungalow-51-Island-Calm-Near-Newport.h92431523.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/108000000/107640000/107630500/107630402/5687f6d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/108000000/107640000/107630500/107630402/w1216h1624x0y0-66b80400.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books, video library](https://images.trvl-media.com/lodging/108000000/107640000/107630500/107630402/69327ef3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/108000000/107640000/107630500/107630402/e13c8280.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Furnished & Flexible – Perfect for Longer Stays in Dartmouth, MA! Dartmouth CA $165 CA $428 total includes taxes & fees Oct 31 - Nov 1 [](https://www.expedia.ca/North-Dartmouth-Hotels-Charming-1-Bedroom-House-With-AC-And-WiFi-In-Dartmouth-Close-To-Buttonwood-Park.h107630402.Hotel-Information) ![TV, fireplace](https://images.trvl-media.com/lodging/116000000/115160000/115155900/115155816/ec92862e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/116000000/115160000/115155900/115155816/476b1d9c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/116000000/115160000/115155900/115155816/de28f5ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/116000000/115160000/115155900/115155816/afac6491.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ellery Beach Bungalow #45- A Refined Island Escape Middletown 10/10 Exceptional (1) "Beautiful area, walking distance to the beach and restaurants, nice clean house" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dana N. CA $158 CA $624 total includes taxes & fees Nov 18 - Nov 19 [](https://www.expedia.ca/Middletown-Hotels-Ellery-Beach-Bungalow-45-A-Refined-Island-Escape.h115155816.Hotel-Information) ![Beach nearby, beach towels](https://images.trvl-media.com/lodging/45000000/44790000/44788900/44788859/2e8c2b33.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/45000000/44790000/44788900/44788859/b39967ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/45000000/44790000/44788900/44788859/2e4456f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/45000000/44790000/44788900/44788859/a610c782.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### ☼ Westport Point ☼ beach house on 1/2 acre easy access to beach/historic village Westport 9.8/10 Exceptional (21) "We enjoyed our stay and recommend It. Delightful back yard and patio area and a very pleasant front porch." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alan M. CA $194 CA $592 total includes taxes & fees Nov 6 - Nov 7 [](https://www.expedia.ca/Westport-Point-Hotels-Westport-Point-Beach-House-On-12-Acre-Easy-Access-To-Beachhistoric-Village.h44788859.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/79000000/78750000/78741400/78741380/8b2e390c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/79000000/78750000/78741400/78741380/e2084987.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/79000000/78750000/78741400/78741380/dcdc8712.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, DVD player](https://images.trvl-media.com/lodging/79000000/78750000/78741400/78741380/e22d1060.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beach house walking distance to Second Beach Easton's Point 9.8/10 Exceptional (24) "Excellent communication with Peter before arrival and during our stay. The house and outdoor space was terrific for our party of 6, a short walk to the beach and into town. Would love to return in the future. Thank you! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lauren A. CA $251 CA $739 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Middletown-Hotels-Beach-House-Walking-Distance-To-Second-Beach.h78741380.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/104000000/103440000/103432500/103432449/96bbef47.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/104000000/103440000/103432500/103432449/1d87e5db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/104000000/103440000/103432500/103432449/d035a3b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/104000000/103440000/103432500/103432449/10cc10c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Little Creek Retreat - RIBryan Property Middletown 9.4/10 Exceptional (13) "Although my party and I only stayed for 1 night we still had a great time in this lovely house." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Vincent M. CA $337 CA $933 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Middletown-Hotels-Little-Creek-Retreat-RIBryan-Property.h103432449.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) ![Dining](https://images.trvl-media.com/lodging/49000000/48490000/48483300/48483278/1925ab75.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/49000000/48490000/48483300/48483278/76fe1a2e.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) ### 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." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Swathanthra M. CA $769 CA $1,695 total includes taxes & fees Oct 25 - Oct 26 [](https://www.expedia.ca/Oak-Bluffs-Hotels-MOST-CHIC-SPOT-Your-Marthas-Vineyard-Getaway.h48483278.Hotel-Information) ![Highchair](https://images.trvl-media.com/lodging/95000000/94870000/94870000/94869907/cf095dcc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/95000000/94870000/94870000/94869907/cbacbb68.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/95000000/94870000/94870000/94869907/466956bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/95000000/94870000/94870000/94869907/75d8fb14.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Half mile to beach, Family & Pet Friendly, Newly Renovated Full House Middletown 10/10 Exceptional (18) "Great property in a convenient location. Highly recommend this home. Property manager was great at getting back to us. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jim C. CA $350 CA $1,036 total includes taxes & fees Nov 20 - Nov 21 [](https://www.expedia.ca/Middletown-Hotels-Half-Mile-To-Beach.h94869907.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/97000000/96350000/96347500/96347420/b1abb2c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/97000000/96350000/96347500/96347420/c234b091.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/97000000/96350000/96347500/96347420/e678f734.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/97000000/96350000/96347500/96347420/w1090h718x0y0-94558ab4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Stones Throw Waterfront Dartmouth 8.8/10 Excellent (6) "According to the listing, the property has AC. That is not true. It had a tiny portable unit that wasn't on when we entered and didn't cool once it was turned on. It also had a window unit that had no place to plug in. There were bugs in multiple areas. The property was not habitable, so we ended up booking a hotel room in a nearby town. VRBO compensated us partially but the owner was unwilling to refund any of our money even though we did not stay in the property. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ashley R. CA $276 CA $799 total includes taxes & fees Oct 25 - Oct 26 [](https://www.expedia.ca/South-Dartmouth-Hotels-Stones-Throw-Waterfront.h96347420.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/79000000/78190000/78183300/78183300/dbe99d9d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/79000000/78190000/78183300/78183300/5218f616.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/79000000/78190000/78183300/78183300/f462c27f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/79000000/78190000/78183300/78183300/c6b79c2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### NEW! Renovated Family-Friendly Vineyard Haven Home, Close to town! Tisbury 10/10 Exceptional (16) "The house is beautiful and conveniently located. The host, Melissa, was accessible and super helpful. We thoroughly enjoyed our time here and hope to be back in the future." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Betel G. CA $727 CA $1,553 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Vineyard-Haven-Hotels-NEW-Renovated-Family-Friendly-Vineyard-Haven-Home.h78183300.Hotel-Information) ![Sun loungers, beach towels](https://images.trvl-media.com/lodging/34000000/33710000/33705200/33705139/f87fa2ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/34000000/33710000/33705200/33705139/31b0a8e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/34000000/33710000/33705200/33705139/022a5a12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33710000/33705200/33705139/cd443f18.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Historic Captains House - Newly Renovated Primary Bathroom and Upgraded Kitchen West Tisbury 10/10 Exceptional (57) "Perfect spot for a low key family vacation in MV. The hosts were amazing too. Sad to leave!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ryan U. CA $1,329 CA $2,616 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Vineyard-Haven-Hotels-Historic-Captains-House-Newly-Renovated-Primary-Bathroom-And-Upgraded-Kitchen.h33705139.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/103000000/102860000/102852300/102852293/aee30659.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/103000000/102860000/102852300/102852293/02ffb52f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/103000000/102860000/102852300/102852293/c8592884.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/103000000/102860000/102852300/102852293/9218d955.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Beach Estate, Panoramic Ocean Views, 5700 sqft Mattapoisett 9.8/10 Exceptional (7) "This was the perfect getaway for our large family. Everything was immaculate and we had all the comforts of home. We had a great week!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Catherine T. CA $867 CA $2,381 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Mattapoisett-Hotels-The-Beachfront-Estate.h102852293.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/104000000/103440000/103431300/103431272/w1280h849x0y4-97fa4ddb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, computer monitors](https://images.trvl-media.com/lodging/104000000/103440000/103431300/103431272/874580bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/104000000/103440000/103431300/103431272/w1277h848x3y5-6702167a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/104000000/103440000/103431300/103431272/w1276h853x4y0-6779aa33.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Middletown Bungalow - RIBryan Property Middletown 9.4/10 Exceptional (13) "Wonderful house and great location!! Super responsive host. Great vacation, thank you!!! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kristen P. CA $422 CA $953 total includes taxes & fees Nov 17 - Nov 18 [](https://www.expedia.ca/Middletown-Hotels-Middletown-Modern-Bungalow-RIBryan-Property.h103431272.Hotel-Information) ![4 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/105000000/104150000/104141900/104141861/135ba2ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/105000000/104150000/104141900/104141861/w1137h737x0y3-8e7c3a3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/105000000/104150000/104141900/104141861/4813bd07.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/105000000/104150000/104141900/104141861/fe6ff6da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Scenic 4BR/3BA Waterfront Getaway with private dock, kayaks & Stunning Views Dartmouth 10/10 Exceptional (13) "Beautiful home, well maintained, incredibly hospitable and responsive host. Kitchen is well equipped and amply stocked with cooking essential and extras for feeding your guests. Wonderful spacious yard great for outdoor fun." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nick R. CA $1,118 CA $1,892 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/South-Dartmouth-Hotels-Cozy.h104141861.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/101000000/100540000/100530500/100530404/w1020h678x4y4-ad2a541d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/101000000/100540000/100530500/100530404/w1020h678x4y4-79c381f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/101000000/100540000/100530500/100530404/w1024h678x0y4-c5e2e4ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/101000000/100540000/100530500/100530404/w1017h678x4y4-3bed50d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Allston Greens Summar Middletown 10/10 Exceptional (9) "The house was spotless, the beds were clean and comfortable, kitchen well stocked, nice details like beach chairs and towels, little extra bathroom supplies, the lower level was perfect for the teenagers. The lower kitchen was great for family gathering, the backyard was fenced and awesome. We appreciated the large outdoor table and seating area around the fire table. Overall a fantastic stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rebecca S. CA $491 CA $1,343 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Middletown-Hotels-Allston-Greens-Summar.h100530404.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/55000000/54940000/54935300/54935241/w2388h1514x0y77-1097f3b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Video games, books, video library](https://images.trvl-media.com/lodging/55000000/54940000/54935300/54935241/w2323h1742x204y153-3585a9ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/55000000/54940000/54935300/54935241/a1cc2110.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/55000000/54940000/54935300/54935241/0fb3af2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beautiful Estate with salt water pool & pond with kayaks Oak Bluffs CA $3,497 CA $5,653 total includes taxes & fees Oct 25 - Oct 26 [](https://www.expedia.ca/Oak-Bluffs-Hotels-Beautiful-Estate-With-Salt-Water-Pool-Pond-With-Kayaks.h54935241.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/77000000/76160000/76155400/76155312/9ed34572.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/77000000/76160000/76155400/76155312/49aa95b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/77000000/76160000/76155400/76155312/5462b7b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/77000000/76160000/76155400/76155312/87ab56ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Stunning, Chic Remodel! Beach House Minutes to Newport! Middletown 9.8/10 Exceptional (18) "The house was convientky close to Newport There were 6 adults with us plenty of space for everyone. Host was very responsive And accommodating. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kristen K. CA $1,469 CA $2,846 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Middletown-Hotels-Stunning.h76155312.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=2025-11-07&endDate=2025-11-08®ionId=3000441000&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&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-Private-Vacation-Homes.d3000441000-aaPrivateVacationHomes.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FCuttyhunk-Private-Vacation-Homes.d3000441000-aaPrivateVacationHomes.Travel-Guide-Accommodation) ## Top Cuttyhunk Hotel Reviews ![Whaler Inn and Suites](//images.trvl-media.com/lodging/1000000/30000/27500/27418/d818de32_y.jpg) ### Whaler Inn and Suites 10/10 Excellent "Hot tub was great. Had a good time unwinding. " [](https://expedia.ca/New-Bedford-Hotels-Whaler-Inn-And-Suites.h27418.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 "Amazing location with awesome amenities and views. Also very close to the bus stop!" [](https://expedia.ca/Newport-Hotels-The-East-Island-Reserve-Hotel.h17443695.Hotel-Information) ![Baymont by Wyndham North Dartmouth / Fall River](//images.trvl-media.com/lodging/1000000/20000/13800/13758/f635e897_y.jpg) ### Baymont by Wyndham North Dartmouth / Fall River 10/10 Excellent "I have been coming to this hotel for over 5 years and I wouldn't stay any other place. I visit from Florida and Massachusetts is my hometown, but this particular hotel is like my second home. The managers Anthony and Joy go above and beyond to make your stay pleasant and are very courteous and caring people. You are in walking distance from everything the local mall, gas stations, shopping marts, retail stores, and restaurants just perfect for a quick getaway and it makes it even more for a comfortable stay 😚" [](https://expedia.ca/North-Dartmouth-Hotels-Baymont-By-Wyndham-North-Dartmouth.h13758.Hotel-Information) ![Best Western Dartmouth-New Bedford](//images.trvl-media.com/lodging/2000000/1540000/1535900/1535858/3263a0b3_y.jpg) ### Best Western Dartmouth-New Bedford 10/10 Excellent "The front desk staff were so nice and accommodating. We will stay at this facility again when traveling to Massachusetts to visit our grandchildren" [](https://expedia.ca/North-Dartmouth-Hotels-Best-Western-Dartmouth-New-Bedford.h1535858.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 "Clean room" [](https://expedia.ca/Falmouth-Hotels-Hotel-Cape-Cod.h11989.Hotel-Information) ![Hampton Inn by Hilton New Bedford/Fairhaven](//images.trvl-media.com/lodging/1000000/60000/55000/54948/647c4f15_y.jpg) ### Hampton Inn by Hilton New Bedford/Fairhaven 10/10 Excellent "This is my favorite hotel in the area" [](https://expedia.ca/Fairhaven-Hotels-Hampton-Inn-By-Hilton-New-BedfordFairhaven.h54948.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 "We stayed here for an overnight and were pleasantly surprised by this motel. It is a basic accommodation, but very clean with a comfortable bed free coffee, great location and very reasonably priced. We will certainly stay here again in the future. Highly recommend it for the price!" [](https://expedia.ca/Vineyard-Haven-Hotels-Vineyard-Harbor-Motel.h60384563.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 "Nice Room!" [](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 "Hotel is very nice and clean in a great location. Easy parking. Would love to come back again. " [](https://expedia.ca/Newport-Hotels-Wyndham-Newport-Hotel.h1101766.Hotel-Information) ## Find out more about Cuttyhunk ## Cuttyhunk Vacation Homes information | Number of reviews | | | --- | --- | | Accommodation | Vacation Homes | | Lowest Price | | | Highest Price | | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - More ways to book - [4 Star Hotels in Bliss Corner](https://www.expedia.ca/4Star-Bliss-Corner-Hotels.s40-0-d553248635976386960.Travel-Guide-Filter-Hotels) - [Aparthotels in Aquinnah](https://www.expedia.ca/Aquinnah-Apart-Hotels.d553248634998599060-aaApartHotels.Travel-Guide-Accommodation) - [B&B in Aquinnah](https://www.expedia.ca/Aquinnah-Bed-And-Breakfast.d553248634998599060-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Hotels near Aquinnah Cliffs](https://www.expedia.ca/Aquinnah-Cliffs-Hotels.0-l6091789-0.Travel-Guide-Filter-Hotels) - [Guest Houses in Aquinnah](https://www.expedia.ca/Aquinnah-Guest-Houses.d553248634998599060-aaGuestHouses.Travel-Guide-Accommodation) - 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