Title: 4 Stars Hotels in Osterville, Massachusetts from CA $189 - Find Cheap Osterville Hotels With 4 Stars | Expedia.ca [Osterville Travel Guide](https://expedia.ca/Osterville.dx183338)[Hotels in Osterville](https://expedia.ca/Osterville-Hotels.d183338.Travel-Guide-Hotels)[Vacation Rentals in Osterville](https://expedia.ca/Osterville-Vacation-Rentals.d183338.Travel-Guide-VacationRentals)[Flights to Osterville](https://expedia.ca/Cheap-Flights-To-Osterville.d183338.Travel-Guide-Flights)[Osterville Car Rentals](https://expedia.ca/Car-Rentals-In-Osterville.d183338.Car-Rental-Guide)[Osterville Vacation Packages](https://expedia.ca/Osterville.d183338.Destination-Travel-Guides) ![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/486000/486619-osterville.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # 4 Stars Hotels in Osterville, Massachusetts from CA $189 ![](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 availability on Osterville 4 Star Hotels Tonight [Oct 14 - Oct 15](https://www.expedia.ca/Hotel-Search?regionId=183338&startDate=2025-10-14&endDate=2025-10-15&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 15 - Oct 16](https://www.expedia.ca/Hotel-Search?regionId=183338&startDate=2025-10-15&endDate=2025-10-16&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=183338&startDate=2025-10-17&endDate=2025-10-19&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=183338&startDate=2025-10-24&endDate=2025-10-26&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Osterville 4 Star Hotels ![Outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/20000/12900/12897/b57e0b1f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/12900/12897/b82acf26.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/20000/12900/12897/e05c3d69.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/20000/12900/12897/0ad12b76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Margaritaville Resort Cape Cod Hyannis 8.6/10 Excellent (379) "Very nice place to stay " CA $179 CA $285 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Hyannis-Hotels-Cape-Codder-Resort-And-Spa.h12897.Hotel-Information) ![Reception](https://images.trvl-media.com/lodging/50000000/49180000/49175900/49175859/3458b4d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, in-room safe, individually decorated](https://images.trvl-media.com/lodging/50000000/49180000/49175900/49175859/ad80c566.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/50000000/49180000/49175900/49175859/3348b4c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/50000000/49180000/49175900/49175859/de3c9577.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### AutoCamp Cape Cod Falmouth 9.4/10 Exceptional (294) "Airstream trailer was efficient and fun, the grounds and clubhouse excellent " CA $197 CA $281 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Falmouth-Hotels-AutoCamp-Cape-Cod.h49175859.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/50000/40500/40461/9f940314.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Daily cooked-to-order breakfast for a fee](https://images.trvl-media.com/lodging/1000000/50000/40500/40461/cddd593a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/50000/40500/40461/2de66a76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Two Double Beds](https://images.trvl-media.com/lodging/1000000/50000/40500/40461/85ee8ddf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Doubletree by Hilton Cape Cod - Hyannis Hyannis 8.4/10 Very good (865) "Great location, awesome area for amenities, delicious cookies, as usual!" CA $165 CA $189 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Hyannis-Hotels-Doubletree-By-Hilton-Cape-Cod-Hyannis.h40461.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/10000/8000/7948/5d8fbc52.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private beach, sun loungers, beach umbrellas, beach towels](https://images.trvl-media.com/lodging/1000000/10000/8000/7948/cb01c753.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, desk, iron/ironing board, free cribs/infant beds](https://images.trvl-media.com/lodging/1000000/10000/8000/7948/96ca76a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 indoor pools, 3 outdoor pools, sun loungers](https://images.trvl-media.com/lodging/1000000/10000/8000/7948/3c08c6f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Mansion at Ocean Edge Brewster 8.2/10 Very good (1000) "Amazing stay and location! " CA $272 CA $360 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Brewster-Hotels-The-Mansion-At-Ocean-Edge.h7948.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/10000000/9390000/9387800/9387761/8146a59e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor spa tub](https://images.trvl-media.com/lodging/10000000/9390000/9387800/9387761/b7217352.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Body treatments, hot stone massages, deep-tissue massages](https://images.trvl-media.com/lodging/10000000/9390000/9387800/9387761/bcb652a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor wedding](https://images.trvl-media.com/lodging/10000000/9390000/9387800/9387761/56327e61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Mirbeau Inn & Spa Plymouth 9.6/10 Exceptional (443) "The Spa was luxurious. Had a great birthday spa day, lunch, dinner and night stay with my girlfriend! " CA $430 CA $533 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Plymouth-Hotels-Mirbeau-Inn-Spa.h9387761.Hotel-Information) ![Front of property - evening/night](https://images.trvl-media.com/lodging/1000000/700000/694900/694842/2026bafa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Courtyard](https://images.trvl-media.com/lodging/1000000/700000/694900/694842/cfebdb4e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/700000/694900/694842/df7034df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Suite, 1 Bedroom, Balcony | Living room](https://images.trvl-media.com/lodging/1000000/700000/694900/694842/567c97f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vineyard Square Hotel & Suites Edgartown 9.2/10 Wonderful (304) "Beautiful property. Would stay here again. " CA $242 CA $270 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/Edgartown-Hotels-Vineyard-Square-Hotel-Suites.h694842.Hotel-Information) ![Seasonal outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/7000000/6170000/6165700/6165614/cb9a8399.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/7000000/6170000/6165700/6165614/29e47360.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/7000000/6170000/6165700/6165614/f546da25.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/7000000/6170000/6165700/6165614/0959237c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Winstead Inn Harwich 9.4/10 Exceptional (125) "Windstead Inn is a beautiful property!! Management was great, let us check in early and our room was upgraded. Would definitely stay again." CA $236 CA $286 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Harwich-Hotels-Winstead-Inn.h6165614.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/106000000/105950000/105944400/105944312/c684860e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, premium bedding, pillowtop beds, individually decorated](https://images.trvl-media.com/lodging/106000000/105950000/105944400/105944312/6a0d52e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/106000000/105950000/105944400/105944312/5ba9d892.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach/ocean view](https://images.trvl-media.com/lodging/106000000/105950000/105944400/105944312/ac86cf96.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Starlight Lodge Cape Cod Dennis 8.2/10 Very good (25) "Good spot, filled our needs would return" [](https://www.expedia.ca/Dennis-Hotels-Starlight-Lodge-Cape-Cod.h105944312.Hotel-Information) ![Front of property - evening/night](https://images.trvl-media.com/lodging/7000000/6290000/6289200/6289195/0019f2a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Executive King Room](https://images.trvl-media.com/lodging/7000000/6290000/6289200/6289195/cd29befb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/7000000/6290000/6289200/6289195/0d18182b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Executive King Room](https://images.trvl-media.com/lodging/7000000/6290000/6289200/6289195/30c286f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Inn At Cape Cod Yarmouth Port 9.6/10 Exceptional (89) "I thought the property was one of the best on the Cape having stayed in many. Service was great and room was wonderful." CA $388 CA $445 total includes taxes & fees Oct 21 - Oct 22 [](https://www.expedia.ca/Yarmouth-Port-Hotels-The-Inn-At-Cape-Cod.h6289195.Hotel-Information) ![Luxury Suite, 1 King Bed, Jetted Tub, Garden Area | Terrace/patio](https://images.trvl-media.com/lodging/10000000/9830000/9823200/9823150/46b131b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/10000000/9830000/9823200/9823150/337fd3ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Suite, 1 King Bed, Jetted Tub, Garden Area](https://images.trvl-media.com/lodging/10000000/9830000/9823200/9823150/fd3dec4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/10000000/9830000/9823200/9823150/0c5dbc91.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Candleberry Inn on Cape Cod Brewster 10/10 Exceptional (139) "Stunning bed and breakfast. Amazing owners and a experience you won’t forget." CA $406 CA $464 total includes taxes & fees Oct 28 - Oct 29 [](https://www.expedia.ca/Brewster-Hotels-Candleberry-Inn-On-Cape-Cod.h9823150.Hotel-Information) ![View from room](https://images.trvl-media.com/lodging/2000000/1950000/1948000/1947981/36981e2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/2000000/1950000/1948000/1947981/0d6f5ad6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Salt Pond Room](https://images.trvl-media.com/lodging/2000000/1950000/1948000/1947981/25945a89.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior entrance](https://images.trvl-media.com/lodging/2000000/1950000/1948000/1947981/0f3d46d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Inn at Yarmouth Port Yarmouth Port 9.6/10 Exceptional (119) "We liked everything, the hosts were amazing and helpful, breakfasts top-notch, great climate control in the room, modern comfort in historic setting" CA $403 CA $461 total includes taxes & fees Nov 5 - Nov 6 [](https://www.expedia.ca/Yarmouth-Port-Hotels-The-Inn-At-Yarmouth-Port.h1947981.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/27000000/26510000/26506800/26506782/40379add.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/27000000/26510000/26506800/26506782/a578dbd5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Flat-screen TV](https://images.trvl-media.com/lodging/27000000/26510000/26506800/26506782/cd0d1e2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private beach, white sand, sun loungers, beach umbrellas](https://images.trvl-media.com/lodging/27000000/26510000/26506800/26506782/26293cb8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Winstead Beach Resort Harwich Port 9.2/10 Wonderful (60) "Very nice hotel, staff. Great location for relaxing visit to the mountains. " CA $299 CA $362 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/Harwich-Port-Hotels-Winstead-Beach-Resort.h26506782.Hotel-Information) ![View from property](https://images.trvl-media.com/lodging/3000000/2740000/2732700/2732648/6f0f3611.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property - evening/night](https://images.trvl-media.com/lodging/3000000/2740000/2732700/2732648/a1617bcc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/3000000/2740000/2732700/2732648/1ffa4caa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Flat-screen TV, DVD player](https://images.trvl-media.com/lodging/3000000/2740000/2732700/2732648/3cf5ff2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Old Manse Inn Brewster 9.8/10 Exceptional (251) "The Old Manse Inn is amazing and everything they advertise! " CA $328 CA $376 total includes taxes & fees Nov 5 - Nov 6 [](https://www.expedia.ca/Brewster-Hotels-The-Old-Manse-Inn.h2732648.Hotel-Information) ![Luxury King Room ](https://images.trvl-media.com/lodging/27000000/26470000/26468700/26468676/c0638e2f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/27000000/26470000/26468700/26468676/b45ea86c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily full breakfast](https://images.trvl-media.com/lodging/27000000/26470000/26468700/26468676/03963e2f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/27000000/26470000/26468700/26468676/f8a15f92.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sea Street Inn Hyannis 9.8/10 Exceptional (45) "Very nicely renovated small property with a fantastic breakfast." CA $347 CA $397 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Hyannis-Hotels-Sea-Street-Inn.h26468676.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/35000000/34280000/34270900/34270883/b6788ae2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/35000000/34280000/34270900/34270883/90eb51ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, travel crib, WiFi, bed sheets](https://images.trvl-media.com/lodging/35000000/34280000/34270900/34270883/9f64694e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, Netflix, DVD player, books](https://images.trvl-media.com/lodging/35000000/34280000/34270900/34270883/1e0550a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### New to Market Cape Cod Waterfront Gem 1 Mile from Ocean, Boating from Backyard West Dennis [](https://www.expedia.ca/West-Dennis-Hotels-New-To-Market-Cape-Cod-Waterfront-Gem-1-Mile-From-Ocean.h34270883.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/34000000/33650000/33643500/33643482/cc0f97f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33650000/33643500/33643482/8b73b221.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/34000000/33650000/33643500/33643482/0e148397.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, DVD player, books](https://images.trvl-media.com/lodging/34000000/33650000/33643500/33643482/5976a9b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Breathtaking Waterviews with Private Beach - Harbour House with AC and Heat Oak Bluffs 10/10 Exceptional (13) "We had a lovely quiet week at Harbour House. It's a very clean well maintained beach house, nothing fancy but it has everything you could possibly need. The owners were easy to contact about any details or concerns. Great sunrise views, several nice walks available from the house, easy driving distance to everything else. It was a big place for just two of us but the location made it worthwhile. We would definitely stay again." [](https://www.expedia.ca/Oak-Bluffs-Hotels-Breathtaking-Waterviews-With-Private-Beach-Harbour-House-With-AC-And-HEAT.h33643482.Hotel-Information) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/38000000/37010000/37009900/37009839/5ba03a06.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/38000000/37010000/37009900/37009839/w1284h954x0y0-9be17448.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/38000000/37010000/37009900/37009839/091e18f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sun loungers, beach towels](https://images.trvl-media.com/lodging/38000000/37010000/37009900/37009839/b8bb7a87.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### We are back! Exceptional home 3min to bike path,beach,restaurants. Private pool North Falmouth 9.8/10 Exceptional (10) "Very responsive owners. Good location. We enjoyed our time there." [](https://www.expedia.ca/North-Falmouth-Hotels-We-Are-Back-Exceptional-Home-3min-To-Bike-Path.h37009839.Hotel-Information) ![BBQ/picnic area](https://images.trvl-media.com/lodging/14000000/13210000/13209500/13209405/e985b92c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/14000000/13210000/13209500/13209405/df7fcc54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![40-inch Smart TV with cable channels, TV](https://images.trvl-media.com/lodging/14000000/13210000/13209500/13209405/f537ec08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/14000000/13210000/13209500/13209405/51d79d64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Platinum Pebble Boutique Inn - Adults Only West Harwich 9.8/10 Exceptional (23) "We had a wonderful stay,Shaun and Sharon were so helpful, wanting to ensure we got the most out of our trip. The breakfasts were a highlight, delicious xx" [](https://www.expedia.ca/West-Harwich-Hotels-The-Platinum-Pebble-Boutique-Inn-Adults-Only.h13209405.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/2000000/1160000/1159200/1159118/c2ed8a3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property entrance](https://images.trvl-media.com/lodging/2000000/1160000/1159200/1159118/3b0ad9d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1160000/1159200/1159118/54fdf702.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool](https://images.trvl-media.com/lodging/2000000/1160000/1159200/1159118/a6b80711.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Brewster by the Sea Inn West Brewster 9.8/10 Exceptional (169) "Spacious comfortable stylish room. Gourmet breakfast. Congenial host/owner." CA $504 CA $576 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Brewster-Hotels-Brewster-By-The-Sea-Inn.h1159118.Hotel-Information) ![Outdoor pool, open 7:00 AM to 7:00 PM, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/12000000/11700000/11698200/11698147/b81a642b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, 1 King Bed (Private Porch)](https://images.trvl-media.com/lodging/12000000/11700000/11698200/11698147/093a07ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, 1 King Bed (Private Porch)](https://images.trvl-media.com/lodging/12000000/11700000/11698200/11698147/ab0949a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/12000000/11700000/11698200/11698147/39a30658.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Captain Freeman Inn Brewster 10/10 Exceptional (70) "The room I stayed in was gorgeous. " [](https://www.expedia.ca/Brewster-Hotels-Captain-Freeman-Inn.h11698147.Hotel-Information) ![](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%2F4Star-Osterville-Hotels.s40-0-d183338.Travel-Guide-Filter-Hotels)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2F4Star-Osterville-Hotels.s40-0-d183338.Travel-Guide-Filter-Hotels) ## Explore similar 5-star hotels Many 5-star hotels have the same amenities as 4-star hotels. See all 5-star hotels in Osterville. ![Harbor View Hotel](https://images.trvl-media.com/lodging/1000000/10000/8600/8504/7b9d68f4_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Harbor View Hotel 131 N Water Street Marthas Vineyard, Edgartown, MA CA $373 CA $441 total Nov 2 - Nov 3 includes taxes & fees 8.8/10 Excellent! (1,002 reviews) [](https://expedia.ca/Edgartown-Hotels-Harbor-View-Hotel.h8504.Hotel-Information) Still don't see what you're looking for? [See all properties in Osterville.](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=15%2F10%2F2025&endDate=16%2F10%2F2025®ionId=183338&star=40) You can also use these popular filters to refine your search. [Pool](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=15%2F10%2F2025&endDate=16%2F10%2F2025®ionId=183338&star=40&star=40&amenities=POOL)[Spa](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=15%2F10%2F2025&endDate=16%2F10%2F2025®ionId=183338&star=40&star=40&amenities=SPA_ON_SITE)[Hot tub](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=15%2F10%2F2025&endDate=16%2F10%2F2025®ionId=183338&star=40&star=40&amenities=HOT_TUB)[Breakfast included](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=15%2F10%2F2025&endDate=16%2F10%2F2025®ionId=183338&star=40&star=40&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=15%2F10%2F2025&endDate=16%2F10%2F2025®ionId=183338&star=40&star=40&amenities=WATER_PARK) 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. ## Learn more about Osterville Elegant boutiques and seafood restaurants line Main Street in this charming Cape Cod village with New England coastal appeal. Spend sunny afternoons at Joshua's Pond or Dowses Beach, where calm waters welcome swimmers and kayakers. [See all hotels in Osterville](https://www.expedia.ca/Hotel-Search?startDate=2025-10-28&endDate=2025-10-29&adults=2®ionId=183338) ![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/486000/486619-osterville.jpg?impolicy=fcrop&w=900&h=506&p=1&q=high) ## Top Osterville Hotel Reviews ![Margaritaville Resort Cape Cod](//images.trvl-media.com/lodging/1000000/20000/12900/12897/b57e0b1f_y.jpg) ### Margaritaville Resort Cape Cod 10/10 Excellent "Rooms were recently renovated and very comfortable. We had requested adjoining rooms for my family of five. When we checked in we were told the rooms were adjoining, they were not and we were unable to move to another accommodation that would allow us all to stay together. That was a definite disappointment that we had to split up our family. " [](https://expedia.ca/Hyannis-Hotels-Cape-Codder-Resort-And-Spa.h12897.Hotel-Information) ## Find out more about Osterville If you’re looking for a spot with great rates, just-for-you amenities, and a world of luxurious little perks, the best 4 Stars hotels in Osterville are calling your name. Known for providing first-rate service in amazing locations, each of the Osterville 4 Stars hotels lets discerning travelers bask in an unforgettable experience. Kick back in your spacious room. Relax in the lobby’s sumptuous surroundings. Start the day with delicious room service, and then use the complimentary body care items to freshen up before you head out for the day. It’s all waiting for you at the top four star hotels in Osterville. Plus, when you book with Expedia.ca, you might find a cheap deal on a 4 Stars hotel in Osterville, Massachusetts, neighbourhoods near the most popular attractions, so you can see the sights and bask in the discounts all in one trip. Whether you’re planning a romantic retreat or simply want to experience everything the area has to offer, the top Osterville hotels with 4 Stars provide everything you need to unwind in style. ## Frequently asked questions ### What are the best 4-star hotels in Osterville? > Expedia travellers highly recommend [Doubletree by Hilton Cape Cod - Hyannis](https://www.expedia.ca/Hyannis-Hotels-Doubletree-By-Hilton-Cape-Cod-Hyannis.h40461.Hotel-Information). From its handy amenities to its attentive staff, every feature of this 4-star hotel in Osterville is designed to provide an unforgettable vacation experience. ### How much does it cost to stay in a 4-star hotel in Osterville? > We can help you quickly locate the ideal 4-star hotel for your trip to Osterville. Use our filter tool to tailor your search by things like price, amenities and star rating and get access to fantastic deals in a few clicks. > > > > - Search for the lowest price from CA $441 ### What's the difference between 5-star and 4-star hotels in Osterville? > Offering an inviting guest experience and upmarket surroundings, 4-star hotels are an excellent option for your Osterville break. These types of stays generally feature lots of useful amenities that make it simple to unpack and unwind — think 24-hour room service, pools and gyms. Or live in the lap of luxury at a 5-star hotel designed to pamper with exclusive perks and amenities. 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