Title: Chilmark Cottages from CA $614 | Expedia.ca [Hotels in Chilmark](https://expedia.ca/Chilmark-Hotels.d6135676.Travel-Guide-Hotels)[Vacation Rentals in Chilmark](https://expedia.ca/Chilmark-Vacation-Rentals.d6135676.Travel-Guide-VacationRentals)[Things to do in Chilmark](https://expedia.ca/Things-To-Do-In-Chilmark.d6135676.Travel-Guide-Activities)[Chilmark Car Rentals](https://expedia.ca/Car-Rentals-In-Chilmark.d6135676.Car-Rental-Guide)[Chilmark Vacation Packages](https://expedia.ca/Chilmark.d6135676.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/2/92660841fb017fb68076d67660f760a8.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Wen C. # Search Chilmark Cottage Rentals from CA $614 ![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 Next weekend [Sep 26 - Sep 28](https://www.expedia.ca/Hotel-Search?regionId=6135676&startDate=2025-09-26&endDate=2025-09-28&adults=2&lodging=COTTAGE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 3 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=6135676&startDate=2025-10-03&endDate=2025-10-05&adults=2&lodging=COTTAGE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=6135676&startDate=2025-10-17&endDate=2025-10-19&adults=2&lodging=COTTAGE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=6135676&startDate=2025-11-14&endDate=2025-11-16&adults=2&lodging=COTTAGE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Chilmark Cottages ![Exterior](https://images.trvl-media.com/lodging/101000000/100940000/100931500/100931403/12715cb3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![On the beach, sun loungers, beach towels](https://images.trvl-media.com/lodging/101000000/100940000/100931500/100931403/9a123ace.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/101000000/100940000/100931500/100931403/982f62b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/101000000/100940000/100931500/100931403/d268d2b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Maushop Village-Exceptional, 2 bedrooms, Sleeps 4, 1.5 baths, with great views. Mashpee 10/10 Exceptional (30) "We had a great trip and look forward to staying there again. Location is the best part!" [](https://www.expedia.ca/Mashpee-Hotels-4-Race-Point-2-Bedrooms.h100931403.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/37000000/36690000/36683900/36683847/438c57be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/37000000/36690000/36683900/36683847/7fb5dcc3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/37000000/36690000/36683900/36683847/617f51da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sun loungers, beach towels](https://images.trvl-media.com/lodging/37000000/36690000/36683900/36683847/612d31eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beautiful Carriage House on the Chop Oak Bluffs 10/10 Exceptional (24) "Great location, well outfitted, great kitchen, comfortable beds. Would stay again." [](https://www.expedia.ca/Oak-Bluffs-Hotels-Beautiful-Carriage-House-On-The-Chop.h36683847.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/66000000/65420000/65410500/65410429/a4adc50b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby, sun loungers, beach towels](https://images.trvl-media.com/lodging/66000000/65420000/65410500/65410429/w1920h1436x0y4-ba00cb51.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/66000000/65420000/65410500/65410429/0db14160.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/66000000/65420000/65410500/65410429/f8750d75.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Beach Cottage Oak Bluffs 10/10 Exceptional (53) "This was the perfect property for our visit to Martha’s Vineyard. The owners were so responsive and gave us a seamless experience. I would definitely stay at the Cozy Cottage again! " [](https://www.expedia.ca/Oak-Bluffs-Hotels-Cozy-Beach-Cottage.h65410429.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/104000000/103740000/103736300/103736263/e3a28603.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/104000000/103740000/103736300/103736263/53bb224a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, desk, WiFi](https://images.trvl-media.com/lodging/104000000/103740000/103736300/103736263/05479e52.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/104000000/103740000/103736300/103736263/447c2e3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Contemporary cottage with outdoor shower infrared sauna 6 Min drive to the beach Edgartown 9.0/10 Wonderful (2) "Great house with enjoyable blend of spaciousness and cozy appeal. Kitchen was well appointed and great overall aesthetic, layout - roomy for 5. Upstairs suite very open and lots of windows in house. 5 min drive to BREATHTAKING reservation on beach ($20 to park for non members and well worth it), peaceful Japanese gardens nearby too. There's a super cute 500ft ferry ride ($35 round trip) to get to and from this location so plan for food accordingly!" [](https://www.expedia.ca/Edgartown-Hotels-Contemporary-Cottage-With-Outdoor-Shower-Infrared-Sauna-6-Min-Drive-To-The-Beach.h103736263.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/106000000/105880000/105875400/105875346/a6459cc3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby](https://images.trvl-media.com/lodging/106000000/105880000/105875400/105875346/a7f1a505.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/106000000/105880000/105875400/105875346/5122a1fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/106000000/105880000/105875400/105875346/d01e4cb6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming Seaside Cottage Central to the Beach and New Seabury Resort Community Mashpee 9.0/10 Wonderful (13) "Charming village, cute cottage and walking distance to beach and shops." [](https://www.expedia.ca/Mashpee-Hotels-Charming-Seaside-Cottage-Central-To-The-Beach-And-New-Seabury-Resort-Community.h105875346.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/34000000/33160000/33155300/33155218/56ca00c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/34000000/33160000/33155300/33155218/518aeffe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![WiFi, bed sheets](https://images.trvl-media.com/lodging/34000000/33160000/33155300/33155218/c53c1535.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33160000/33155300/33155218/b5043d55.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Make Lasting Memories In This Adorable Vineyard Cottage! Oak Bluffs 9.8/10 Exceptional (150) "Absolutely loved this place. Had everything we needed. Such cute decor. Perfect cute little rental in convenient location. " CA $310 CA $661 total includes taxes & fees Oct 1 - Oct 2 [](https://www.expedia.ca/Oak-Bluffs-Hotels-Make-Lasting-Memories-In-This-Adorable-Vineyard-Cottage.h33155218.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/60000000/59060000/59055600/59055510/0fea7ac2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/60000000/59060000/59055600/59055510/f260d218.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/60000000/59060000/59055600/59055510/c1d70d8b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/60000000/59060000/59055600/59055510/226002f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### LOCATION & QUALITY! Right in town, freshly renovated, near everything u need! Tisbury 10/10 Exceptional (54) "We had a wonderful stay! The place was clean, cute, and very conveniently located. Would definitely return!" [](https://www.expedia.ca/Vineyard-Haven-Hotels-LOCATION-QUALITY-Right-In-Town.h59055510.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/108000000/108000000/107997300/107997278/ad29049f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/108000000/108000000/107997300/107997278/7f904b5e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/108000000/108000000/107997300/107997278/324c2c1f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/108000000/108000000/107997300/107997278/e5963f7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming cottage overlooking the bay in Padanaram Village. Dartmouth 10/10 Exceptional (8) "Beautiful property. The cottage is beautifully decorated and well maintained. Amazing location. Host was very good at communicating. " CA $365 CA $614 total includes taxes & fees Oct 16 - Oct 17 [](https://www.expedia.ca/South-Dartmouth-Hotels-Charming-Cottage-Overlooking-The-Bay-In-Padanaram-Village.h107997278.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/93000000/92330000/92321200/92321106/558431c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/93000000/92330000/92321200/92321106/0a3fbe41.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/93000000/92330000/92321200/92321106/0fdc8e8f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/93000000/92330000/92321200/92321106/c89fc637.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Entire cottage, walk to/from ferry & downtown, newly renovated, parking on site Tisbury 10/10 Exceptional (27) "Perfect for my family of 4. Very walkable to everything Vineyard Haven. " [](https://www.expedia.ca/Vineyard-Haven-Hotels-Entire-Cottage.h92321106.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/73000000/72400000/72396900/72396820/495b6b58.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach](https://images.trvl-media.com/lodging/73000000/72400000/72396900/72396820/2dede53b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/73000000/72400000/72396900/72396820/d8704691.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, dishwasher](https://images.trvl-media.com/lodging/73000000/72400000/72396900/72396820/c12709f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cape Cod cottage with patio - near golf, 100 yards to private Mashpee Beach Mashpee 5.8/10 (28) "Great location and private beach access. Charming enclave perfect for our weekend getaway." [](https://www.expedia.ca/Mashpee-Hotels-Cape-Cod-Cottage-W-Grill-Near-Golf.h72396820.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/28000000/27120000/27117800/27117723/37e0972d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/28000000/27120000/27117800/27117723/921638fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/28000000/27120000/27117800/27117723/925f539a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/28000000/27120000/27117800/27117723/1ec05f29.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming Beach Cottage, Steps To Beach; Ocean Views, Reasonably Priced Mashpee 8.6/10 Excellent (85) "Loved the neighborhood and proximity to the beach and marketplace. Cute space, host was very responsive. Would stay again" [](https://www.expedia.ca/Mashpee-Hotels-Charming-Beach-Cottage.h27117723.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/112000000/111260000/111250400/111250353/28f95427.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/112000000/111260000/111250400/111250353/74f47c02.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach](https://images.trvl-media.com/lodging/112000000/111260000/111250400/111250353/dcc67530.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/112000000/111260000/111250400/111250353/67046550.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Oceanside Cottage with Private Beach Access Mattapoisett 9.8/10 Exceptional (7) "Excellent sea view and very quiet place" [](https://www.expedia.ca/Mattapoisett-Hotels-Oceanside-Cottage-With-Private-Beach.h111250353.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/34000000/33550000/33547700/33547638/1d383a0e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/34000000/33550000/33547700/33547638/94cd3405.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/34000000/33550000/33547700/33547638/9e661f0b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/34000000/33550000/33547700/33547638/f1a0fd2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Spacious Home - 1500 ft from Beach & Circuit Ave Oak Bluffs 10/10 Exceptional (12) "Great stay, clean, great location and Judy the owner was always available if anything came up!" [](https://www.expedia.ca/Oak-Bluffs-Hotels-Spacious-Home-1500-Ft-From-Beach-Circuit-Ave.h33547638.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/36000000/35530000/35525300/35525294/d869d1a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, DVD player](https://images.trvl-media.com/lodging/36000000/35530000/35525300/35525294/bb85288a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sun loungers, beach towels](https://images.trvl-media.com/lodging/36000000/35530000/35525300/35525294/0979f39d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/36000000/35530000/35525300/35525294/fc402096.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### ★The Islander | Steps From Water, Fire Pit, AC★ Mashpee 10/10 Exceptional (51) "We stayed for a sisters weekend and it was just perfect!" [](https://www.expedia.ca/Mashpee-Hotels-The-Islander-Steps-From-Water.h35525294.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/42000000/41940000/41933300/41933271/a3fb0b57.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/42000000/41940000/41933300/41933271/f2c1a391.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/42000000/41940000/41933300/41933271/5863cfd7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/42000000/41940000/41933300/41933271/a783ea64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Small One Bedroom Private Cottage on Large Quiet Property. Tisbury 9.8/10 Exceptional (9) "Absolutely perfect, right down to the brands of soaps and shampoos! Beautiful artwork everywhere. I wouldn't change a thing!" CA $310 CA $511 total includes taxes & fees Oct 12 - Oct 13 [](https://www.expedia.ca/Vineyard-Haven-Hotels-One-Bedroom-Cottage-On-Large-Property-Walking-Distance-To-Vineyard-Haven.h41933271.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/35000000/34980000/34978100/34978037/4dd6c5f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/35000000/34980000/34978100/34978037/ccaee416.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/35000000/34980000/34978100/34978037/9d1816b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/35000000/34980000/34978100/34978037/4813e37f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Private condo in Maushop. Steps to beach, ocean, Popponesset Inn and Marketplace Mashpee 9.6/10 Exceptional (71) "Clean property, great location" [](https://www.expedia.ca/Mashpee-Hotels-Private.h34978037.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/58000000/57240000/57236100/57236011/1c47af9b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/58000000/57240000/57236100/57236011/06760c73.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/58000000/57240000/57236100/57236011/d51f4770.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/58000000/57240000/57236100/57236011/8b6ec15c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cape Cod Cottage steps from Private Beach Mashpee 10/10 Exceptional (39) "Excellent location- we will be back! " [](https://www.expedia.ca/Mashpee-Hotels-Cape-Cod-Cottage-Steps-From-Private-Beach.h57236011.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/33000000/32080000/32075700/32075634/2c0c6090.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books, stereo](https://images.trvl-media.com/lodging/33000000/32080000/32075700/32075634/7c8dbcc9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books, stereo](https://images.trvl-media.com/lodging/33000000/32080000/32075700/32075634/bd71b4c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/33000000/32080000/32075700/32075634/0bc1c522.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### This Romantic Cottage is Simply a Cut Above - Katama 10/10 Exceptional (58) "What a great Cottage. We would stay there again." [](https://www.expedia.ca/Edgartown-Hotels-This-Romantic-Cottage-Is-Simply-A-Cut-Above.h32075634.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/40000000/39960000/39956600/39956527/7afad22c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/40000000/39960000/39956600/39956527/1adf97a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/40000000/39960000/39956600/39956527/dbfaee09.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/40000000/39960000/39956600/39956527/8a3738be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bright and cozy menemsha cottage Chilmark 10/10 Exceptional (5) "Peaceful location near conservation trail and a short drive to Lucy Vincent and the Chilmark Store. Clean, spacious and comfortable for our family of six adults. The owner mailed the key and information about the house ahead of our stay, which was helpful. Highly recommended!" [](https://www.expedia.ca/Chilmark-Hotels-Airey-Two-Bedroom-Menemsha-Cottage.h39956527.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/96000000/95040000/95033200/95033165/fb318ab5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/96000000/95040000/95033200/95033165/47ae3d38.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, oven, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/96000000/95040000/95033200/95033165/9a1a37b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/96000000/95040000/95033200/95033165/5fc0e7f4_edited_c4df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Family Cottage Circuit Ave OB Walk to Everything Oak Bluffs [](https://www.expedia.ca/Oak-Bluffs-Hotels-Cozy-Family-Cottage-Circuit-Ave-OB-Steps-To-Everything.h95033165.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=2025-10-05&endDate=2025-10-06®ionId=6135676&adults=2&lodging=COTTAGE&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%2FChilmark-Cottages.d6135676-aaCottages.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FChilmark-Cottages.d6135676-aaCottages.Travel-Guide-Accommodation) ## Top Chilmark Hotel Reviews ![Falmouth Tides ](//images.trvl-media.com/lodging/70000000/69380000/69374600/69374512/3742adf6_y.jpg) ### Falmouth Tides 10/10 Excellent "I love the location and the room was on the beach. . We came with our dog and we had an amazing time here." [](https://expedia.ca/Falmouth-Hotels-Falmouth-Tides-Motel.h69374512.Hotel-Information) ![Summercamp](//images.trvl-media.com/lodging/11000000/10060000/10058600/10058501/4ff1c19a_y.jpg) ### Summercamp 10/10 Excellent "It was very nice. The room was a little smaller than expected. But we enjoyed our short stay. " [](https://expedia.ca/Oak-Bluffs-Hotels-Summercamp.h10058501.Hotel-Information) ![Falmouth Inn](//images.trvl-media.com/lodging/1000000/900000/893200/893142/a26689a2_y.jpg) ### Falmouth Inn 10/10 Excellent "Was good" [](https://expedia.ca/Falmouth-Hotels-Falmouth-Inn.h893142.Hotel-Information) ![Admiralty Inn & Suites - a Red Collection Hotel](//images.trvl-media.com/lodging/2000000/1280000/1279900/1279850/64d1c0e2_y.jpg) ### Admiralty Inn & Suites - a Red Collection Hotel 10/10 Excellent "I loved habing the indoor and outside pool options. We ×ere also close to the beach." [](https://expedia.ca/Falmouth-Hotels-Admiralty-Inn-Suites.h1279850.Hotel-Information) ![Inn on the Square](//images.trvl-media.com/lodging/1000000/10000/10000/9953/27ed2889_y.jpg) ### Inn on the Square 10/10 Excellent "Very comfortable and clean. " [](https://expedia.ca/Falmouth-Hotels-Inn-On-The-Square.h9953.Hotel-Information) ![Faraway Martha's Vineyard](//images.trvl-media.com/lodging/1000000/70000/65700/65623/10e4fb42_y.jpg) ### Faraway Martha's Vineyard 10/10 Excellent "Great hotel in great location. Restaurants and shopping are right outside your door. We were lucky enough to get a water view from our room. I will definitely be staying there in the future." [](https://expedia.ca/Edgartown-Hotels-Faraway-Marthas-Vineyard.h65623.Hotel-Information) ![Sea Crest Beach Resort](//images.trvl-media.com/lodging/1000000/30000/25600/25567/19fd0067_y.jpg) ### Sea Crest Beach Resort 10/10 Excellent "Beautiful beach. Perfect sand & sea. Buffet breakfast actually well maintaned until the very end. No running out of food. Clean rooms, courteous staff" [](https://expedia.ca/North-Falmouth-Hotels-Sea-Crest-Beach-Hotel.h25567.Hotel-Information) ![Harbor View Hotel](//images.trvl-media.com/lodging/1000000/10000/8600/8504/7b9d68f4_y.jpg) ### Harbor View Hotel 10/10 Excellent "The staff was amazing. Everyone was friendly and willing to help you with anything, from dinner recommendations, sites to see, parking, helping with bags and helping to install the top on my jeep." [](https://expedia.ca/Edgartown-Hotels-Harbor-View-Hotel.h8504.Hotel-Information) ![The Island Inn on Martha's Vineyard](//images.trvl-media.com/lodging/112000000/111560000/111556200/111556199/3615b0cb_y.jpg) ### The Island Inn on Martha's Vineyard 10/10 Excellent "Nice, clean, affordable, and kitchen provided everything for cooking accommodations. Centrally located and walkable to Inkwell and Oak Bluffs center." [](https://expedia.ca/Oak-Bluffs-Hotels-The-Island-Inn.h111556199.Hotel-Information) ## Find out more about Chilmark ## Chilmark Cottages information | Number of reviews | 626 | | --- | --- | | Accommodation | 159 Cottages | | Lowest Price | CA $614 | | Highest Price | CA $661 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - More ways to book - [3 Star Hotels in Martha's Vineyard](https://www.expedia.ca/3Star-Marthas-Vineyard-Hotels.s30-0-d6047691.Travel-Guide-Filter-Hotels) - [4 Star Hotels in Martha's Vineyard](https://www.expedia.ca/4Star-Marthas-Vineyard-Hotels.s40-0-d6047691.Travel-Guide-Filter-Hotels) - [5 Star Hotels in Martha's Vineyard](https://www.expedia.ca/5Star-Marthas-Vineyard-Hotels.s50-0-d6047691.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) - 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