Title: Middletown Cottages from CA $299 | Expedia.ca [Hotels in Middletown](https://expedia.ca/Middletown-Hotels.d8862.Travel-Guide-Hotels)[Vacation Rentals in Middletown](https://expedia.ca/Middletown-Vacation-Rentals.d8862.Travel-Guide-VacationRentals)[Flights to Middletown](https://expedia.ca/Cheap-Flights-To-Middletown.d8862.Travel-Guide-Flights)[Middletown Car Rentals](https://expedia.ca/Car-Rentals-In-Middletown.d8862.Car-Rental-Guide)[Middletown Vacation Packages](https://expedia.ca/Middletown.d8862.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/2/6f9a0e2222ff440d9a1af81a42bdbc0f.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Simmie Reagor # Search Middletown Cottage Rentals from CA $299 ![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 3 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=8862&startDate=2025-10-03&endDate=2025-10-05&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=8862&startDate=2025-11-14&endDate=2025-11-16&adults=2&lodging=COTTAGE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=8862&startDate=2025-12-12&endDate=2025-12-14&adults=2&lodging=COTTAGE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=8862&startDate=2026-01-09&endDate=2026-01-11&adults=2&lodging=COTTAGE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Middletown Cottages ![Exterior](https://images.trvl-media.com/lodging/34000000/33690000/33680200/33680120/5ed3c6fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/34000000/33690000/33680200/33680120/aa45308b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/34000000/33690000/33680200/33680120/310cf1e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, desk, free WiFi, bed sheets](https://images.trvl-media.com/lodging/34000000/33690000/33680200/33680120/5d1eb029.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Direct waterfront renovated cottage. Madison Center 10/10 Exceptional (82) "Beautiful location on water, comfortable cottage " [](https://www.expedia.ca/Madison-Hotels-Direct-Waterfront-Renovated-Cottage.h33680120.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/91000000/91000000/90991500/90991445/65eed284.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/91000000/91000000/90991500/90991445/8e3d5f6a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/91000000/91000000/90991500/90991445/3067f697.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/91000000/91000000/90991500/90991445/2e009ba7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 1-bedroom cottage with Grove Beach 🏖️ access. Clinton 9.2/10 Wonderful (30) "Loved the overall stay and experience. The private beach access is a bonus" CA $141 CA $299 total includes taxes & fees Sep 30 - Oct 1 [](https://www.expedia.ca/Clinton-Hotels-Shalom-Cottage-With-Private-Beach-Rights.h90991445.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/20000000/19670000/19665000/19664948/59a5cbb3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/20000000/19670000/19665000/19664948/89dd225e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/20000000/19670000/19665000/19664948/1fa89ccb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/20000000/19670000/19665000/19664948/eb0e0508.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Go Jump in the Lake! Lebanon 10/10 Exceptional (144) "owner was super nice and the environment was great i would come back " [](https://www.expedia.ca/Lebanon-Hotels-Go-Jump-In-The-Lake.h19664948.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/39000000/38800000/38799200/38799111/0062c9a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/39000000/38800000/38799200/38799111/a961d618.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/39000000/38800000/38799200/38799111/8bb3f14f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/39000000/38800000/38799200/38799111/7dfa7972.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy cottage near downtown Clinton, Marina & Hammonasset Park Clinton 10/10 Exceptional (81) "This was a great property and close to many things to see and visit. The welcome note and goodies were much appreciated. Great communication from the host!!!" [](https://www.expedia.ca/Old-Saybrook-Hotels-New-Cozy-Cottage-Near-Downtown-Clinton-Marina.h38799111.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/89000000/88520000/88510200/88510197/62b9e13d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/89000000/88520000/88510200/88510197/abde5fea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/89000000/88520000/88510200/88510197/b98eb485.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/89000000/88520000/88510200/88510197/db8cb4c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The gardners Cottage 1 mile from long Island Sound - pet friendly Clinton 10/10 Exceptional (17) "Robin was an excellent host and the cottage was beautiful and very well kept! After a very long work day, it was so relaxing to sit in the garden." [](https://www.expedia.ca/Clinton-Hotels-The-Gardners-Cottage-1-Mile-From-Long-Island-Sound-Pet-Friendly.h88510197.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/115000000/114820000/114813800/114813714/2c836889.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/115000000/114820000/114813800/114813714/7f65be79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/115000000/114820000/114813800/114813714/220cd09b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/115000000/114820000/114813800/114813714/w1290h865x0y0-d3852033.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Historic cottage in Deep River, CT Deep River 10/10 Exceptional (1) "Wonderful stay. Charming and perfect. " CA $248 CA $479 total includes taxes & fees Sep 25 - Sep 26 [](https://www.expedia.ca/Deep-River-Hotels-Historic-Cottage-In-Deep-River.h114813714.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/96000000/96000000/95993100/95993075/895dade0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/96000000/96000000/95993100/95993075/dbe5915f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/96000000/96000000/95993100/95993075/0780b9a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/96000000/96000000/95993100/95993075/91f1b1fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly! Lake Pocotopaug 10/10 Exceptional (14) "The place was great and we enjoyed the fishing." [](https://www.expedia.ca/East-Hampton-Hotels-Family-Friendly-Lakeside-Cottage-With-Spectacular-Sunset-Views-Pet-Friendly.h95993075.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/34000000/33560000/33559600/33559588/6fe3e795.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33560000/33559600/33559588/df2db80d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby, sun loungers](https://images.trvl-media.com/lodging/34000000/33560000/33559600/33559588/c0b41082.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/34000000/33560000/33559600/33559588/6a911a11.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Summer Cottage with Water Views at Great Hammock Beach in Old Saybrook Old Saybrook 10/10 Exceptional (64) "Loved the salt marsh with all the birds. The views at the beach were amazing! Scott and Mary-Jo were wonderful! I would definitely stay again!" [](https://www.expedia.ca/Old-Saybrook-Hotels-Summer-Cottage-With-Water-Views-At-Great-Hammock-Beach-In-Old-Saybrook.h33559588.Hotel-Information) ![Cottage (1 Bedroom) | Interior](https://images.trvl-media.com/lodging/95000000/94960000/94956400/94956398/17c78bfe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cottage (1 Bedroom) | Interior](https://images.trvl-media.com/lodging/95000000/94960000/94956400/94956398/d0f664e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cottage (1 Bedroom) | Interior](https://images.trvl-media.com/lodging/95000000/94960000/94956400/94956398/59822060.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cottage (1 Bedroom) | Interior](https://images.trvl-media.com/lodging/95000000/94960000/94956400/94956398/589d3571.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Guilford Carriage House at Granite Lodge! Guilford 9.0/10 Wonderful (2) "I’m normally not one to leave reviews but I had to for The Carriage House! Everything from the homey, relaxing feel to the great views was amazing! My friends and I wanted to extend our stay lol. We’re already planning another stay here for a summer trip! Also appreciated the host’s friendliness and ensuring we had an enjoyable experience. 10/10" [](https://www.expedia.ca/Guilford-Hotels-Guilford-Carriage-House-At-Granite-Lodge.h94956398.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/100000000/99420000/99410600/99410592/bfe4efda.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/100000000/99420000/99410600/99410592/62af3c61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/100000000/99420000/99410600/99410592/d8aa3c37.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/100000000/99420000/99410600/99410592/4399f556.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Adorable Cottage with Cottage porch, walk to water & town Westbrook Center 8.8/10 Excellent (6) "Great host and property" [](https://www.expedia.ca/Westbrook-Hotels-Adorable-Cottage-With-Cottage-Porch.h99410592.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/35000000/34800000/34796500/34796404/08fe8e01.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/35000000/34800000/34796500/34796404/fc84e8f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/35000000/34800000/34796500/34796404/2ad096e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/35000000/34800000/34796500/34796404/6b643501.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 4BR Beach Cottage sits on private beach. Sleeps 12 with comfort, Outdoor grill Westbrook 9.8/10 Exceptional (75) "This was the best place to celebrate my family member’s 60th! Being right on the water was amazing! We enjoyed the outdoor fire pit, the beachy air and the outdoor setting. Inside was clean and adorable. The bunk beds were much larger than appears in the picture. If you want a little getaway to enjoy the salty air, I highly recommend! The owner was very timely in getting back regarding any questions I had and was friendly. " [](https://www.expedia.ca/Westbrook-Hotels-4BR-Beach-Cottage-Sits-On-Private-Beach-Sleeps-12-With-Comfort.h34796404.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/101000000/100440000/100433000/100432991/c42dcdc7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/101000000/100440000/100433000/100432991/a8de3809.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/101000000/100440000/100433000/100432991/2aab4065.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Spices](https://images.trvl-media.com/lodging/101000000/100440000/100433000/100432991/d814ed82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Updated cottage "Beriozka" on Cedar Lake Chester 10/10 Exceptional (12) "Fantastic cottage. Loved the location. Clean well stocked amenities comfy beds. Would definitely stay here again " [](https://www.expedia.ca/Chester-Hotels-Updated-Cottage-Beriozka-On-Cedar-Lake.h100432991.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/100000000/99360000/99356500/99356425/16891ca1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/100000000/99360000/99356500/99356425/65d993ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/100000000/99360000/99356500/99356425/414819e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/100000000/99360000/99356500/99356425/e51f6539.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### A Perfect Getaway. Direct assess to the 1000 acre Old Saybrook Essex Preserve Old Saybrook 10/10 Exceptional (3) "A perfect stay - John and his family were truly wonderful. The house is attached to thier main house, but also very private and secure. We were in town for a wedding weekend and this was the perfect spot for us - truly a beatuiful property! John was helpful in telling us about all of the local spot and supplying us with everything we needed. His wife even welcomed us with a cheese board and wine! Thanks John and family - we had a great time!" [](https://www.expedia.ca/Essex-Hotels-A-Perfect-Getaway-Direct-Assess-To-The-1000-Acre-Old-Saybrook-Essex-Preserve.h99356425.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/76000000/75650000/75645700/75645622/31c19779.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, DVD player, books](https://images.trvl-media.com/lodging/76000000/75650000/75645700/75645622/e1e3f22d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/76000000/75650000/75645700/75645622/1175e0a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/76000000/75650000/75645700/75645622/42e21f28.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Relax with a beautiful lake view Colchester 10/10 Exceptional (21) "Lovely cottage on beautiful Lake Hayward. Very clean, comfortable accommodations and the view of the lake is stunning. The bathroom was newly renovated and the kitchen was well stocked with everything we needed to make and serve our meals. The host was very responsive and kind. Would highly recommend this property and we hope to return soon! " [](https://www.expedia.ca/Colchester-Hotels-Relax-With-A-Beautiful-Lake-View.h75645622.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/111000000/110620000/110614900/110614835/2d485442.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach](https://images.trvl-media.com/lodging/111000000/110620000/110614900/110614835/a7c1b982.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/111000000/110620000/110614900/110614835/26dbbf1a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, dishwasher](https://images.trvl-media.com/lodging/111000000/110620000/110614900/110614835/b7c2c1ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming 3-bedroom cottage in Old Saybrook with AC, WiFi Saybrook Manor 10/10 Exceptional (3) "We had a lovely stay. Everything was as described on the listing and the house had everything we needed for our family. It was great to have the grill and a kitchen with all the supplies needed. The area is lovely and quiet with two small but nice private beaches within walking distance" [](https://www.expedia.ca/Old-Saybrook-Hotels-Charming-3-Bedroom-Cottage-In-Old-Saybrook-With-AC.h110614835.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/38000000/37130000/37121700/37121695/w1024h738x0y3-edd126bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby, sun loungers, beach towels](https://images.trvl-media.com/lodging/38000000/37130000/37121700/37121695/c7f44e03.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, video games, DVD player](https://images.trvl-media.com/lodging/38000000/37130000/37121700/37121695/de41ac64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, video games, DVD player](https://images.trvl-media.com/lodging/38000000/37130000/37121700/37121695/db5a1725.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Adorable New England Cottage, 2 min walk to Beach 🏖️, Available year round Westbrook Center 9.8/10 Exceptional (109) "Cute place, very clean" [](https://www.expedia.ca/Old-Saybrook-Hotels-Comfortable.h37121695.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/34000000/33510000/33507900/33507839/28a14f36.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33510000/33507900/33507839/f3dd647a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/34000000/33510000/33507900/33507839/142f4b2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33510000/33507900/33507839/445ade30.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Waterfront Cottage in Branford branford 10/10 Exceptional (97) "Stunning cottage! Great location. Well-equipped kitchen! Comfy beds. Loved the views! Truly a special place!" [](https://www.expedia.ca/Branford-Hotels-Waterfront-Cottage-In-Branford.h33507839.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/30000000/29850000/29848800/29848752/2394f576.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, books](https://images.trvl-media.com/lodging/30000000/29850000/29848800/29848752/f730e4e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/30000000/29850000/29848800/29848752/d9470cd2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private beach](https://images.trvl-media.com/lodging/30000000/29850000/29848800/29848752/402813ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### DIRECT WATERFRONT PRIVATE BEACH Westbrook Center 9.6/10 Exceptional (24) "This rental was perfect. Super clean and comfy with the most amazing views. Loved that it’s right on the water with a private beach. We will definitely book this property again." [](https://www.expedia.ca/Westbrook-Hotels-DIRECT-WATERFRONT-PRIVATE-BEACH.h29848752.Hotel-Information) ![House (3 Bedrooms) | Front of property](https://images.trvl-media.com/lodging/102000000/101280000/101277200/101277148/ddb0320b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/102000000/101280000/101277200/101277148/67311cc0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/102000000/101280000/101277200/101277148/b38c8b90.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/102000000/101280000/101277200/101277148/6ddf1605.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming Windsor Home w/ Private Backyard! Windsor 8.0/10 Very good (1) "The property was exactly as advertised and what we needed for a two night stay for a graduation. It was economical and accommodated 5 people comfortably. The interior is a bit dated, but clean. We did not spend much time at the property, so it worked well for us. The beds were a bit hard, but functional for two nights." [](https://www.expedia.ca/Windsor-Hotels-Charming-Windsor-Home-W-Private-Backyard.h101277148.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/75000000/74070000/74067100/74067063/76415c98.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/75000000/74070000/74067100/74067063/c0a6e31e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/75000000/74070000/74067100/74067063/31cced8f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books, music library](https://images.trvl-media.com/lodging/75000000/74070000/74067100/74067063/w750h559x0y0-72f30cf0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape Plymouth 10/10 Exceptional (38) "Clean stunning views amazing host " [](https://www.expedia.ca/Plymouth-Hotels-Enjoy-Lakefront-Sunsets-In-Cozy-2BR-Cottage.h74067063.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=8862&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%2FMiddletown-Cottages.d8862-aaCottages.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FMiddletown-Cottages.d8862-aaCottages.Travel-Guide-Accommodation) ## Top Middletown Hotel Reviews ![Red Roof Inn Meriden](//images.trvl-media.com/lodging/1000000/10000/2900/2831/05873179_y.jpg) ### Red Roof Inn Meriden 10/10 Excellent "Management really care about this hotel Is a simple and cheap hotel but you can tell they people running the place they do care and do the best with what they have " [](https://expedia.ca/Hartford-Hotels-Red-Roof-Inn-Meriden.h2831.Hotel-Information) ![The Capitol Hotel](//images.trvl-media.com/lodging/1000000/10000/6800/6777/2c26b973_y.jpg) ### The Capitol Hotel 10/10 Excellent "Good location." [](https://expedia.ca/Hartford-Hotels-The-Capitol-Hotel.h6777.Hotel-Information) ![Omni New Haven Hotel at Yale](//images.trvl-media.com/lodging/1000000/50000/50000/49957/7466af25_y.jpg) ### Omni New Haven Hotel at Yale 10/10 Excellent "Caring Staff + Great Location = Happy Yale Parents We had a great four-night stay while moving our daughter into Yale. The managers truly went above and beyond. At check-in, one manager patiently showed us alternative room options when we were worried about noise, and the room we chose was perfect. Another manager impressed us as well — after we mentioned the tub was slippery and no mat had arrived, he personally went out to buy one for us. The location is unbeatable for visiting Yale, and we loved being able to walk everywhere. The afternoon snacks in the lobby were a nice touch as well. Housekeeping could improve on restocking supplies like coffee pods and coffee cups, but calls to the front desk resolved it quickly. The surrounding neighborhood isn’t the best, though that’s not the hotel’s fault. Overall, excellent service and an ideal location made this a very positive stay. We’d happily return." [](https://expedia.ca/New-Haven-Hotels-Omni-New-Haven-Hotel-At-Yale.h49957.Hotel-Information) ![New Haven Hotel](//images.trvl-media.com/lodging/1000000/40000/36800/36721/dd69cbb4_y.jpg) ### New Haven Hotel 10/10 Excellent "Very walkable" [](https://expedia.ca/New-Haven-Hotels-New-Haven-Hotel.h36721.Hotel-Information) ![Hamden Hotel and Suites – Hamden New Haven](//images.trvl-media.com/lodging/1000000/20000/18000/17931/c3c836db_y.jpg) ### Hamden Hotel and Suites – Hamden New Haven 10/10 Excellent "νονε" [](https://expedia.ca/New-Haven-Hotels-Clarion-Hotel-Suites-Hamden-New-Haven.h17931.Hotel-Information) ![Extended Stay America Suites Hartford Farmington](//images.trvl-media.com/lodging/1000000/160000/151100/151013/02939ae3_y.jpg) ### Extended Stay America Suites Hartford Farmington 10/10 Excellent "Took a chance and so glad I did. Everything was extremely ckean and receptionists were very helpful. Would stay again." [](https://expedia.ca/Hartford-Hotels-Extended-Stay-America-Suites-Hartford-Farmington.h151013.Hotel-Information) ![Motel 6 Wethersfield, CT - Hartford](//images.trvl-media.com/lodging/1000000/990000/986100/986068/692a6601_y.jpg) ### Motel 6 Wethersfield, CT - Hartford 10/10 Excellent "Enjoyed my stay here " [](https://expedia.ca/Hartford-Hotels-Motel-6-Wethersfield.h986068.Hotel-Information) ![Woodspring Suites Newington - Hartford South](//images.trvl-media.com/lodging/106000000/105290000/105285500/105285488/3fbd5164_y.jpg) ### Woodspring Suites Newington - Hartford South 10/10 Excellent "Clean and quiet room " [](https://expedia.ca/Newington-Hotels-Woodspring-Suites-Newington-Hartford-South.h105285488.Hotel-Information) ![Home2 Suites by Hilton East Haven New Haven](//images.trvl-media.com/lodging/1000000/10000/1500/1461/b5c018f9_y.jpg) ### Home2 Suites by Hilton East Haven New Haven 10/10 Excellent "Was a good experience " [](https://expedia.ca/East-Haven-Hotels-Home2-Suites-By-Hilton-East-Haven-New-Haven.h1461.Hotel-Information) ## Find out more about Middletown ## Middletown Cottages information | Number of reviews | 792 | | --- | --- | | Accommodation | 106 Cottages | | Lowest Price | CA $299 | | Highest Price | CA $479 | ## Explore a world of travel with Expedia - 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