Title: Thimble Islands Condo Rentals from CA $105 | Expedia.ca [Thimble Islands Travel Guide](https://expedia.ca/Thimble-Islands.dx6341069)[Hotels in Thimble Islands](https://expedia.ca/Thimble-Islands-Hotels.d6341069.Travel-Guide-Hotels)[Vacation Rentals in Thimble Islands](https://expedia.ca/Thimble-Islands-Vacation-Rentals.d6341069.Travel-Guide-VacationRentals)[Flights to Thimble Islands](https://expedia.ca/Cheap-Flights-To-Thimble-Islands.d6341069.Travel-Guide-Flights)[Thimble Islands Car Rentals](https://expedia.ca/Car-Rentals-In-Thimble-Islands.d6341069.Car-Rental-Guide)[Thimble Islands Vacation Packages](https://expedia.ca/Thimble-Islands.d6341069.Destination-Travel-Guides) ![Default HTG hotel image](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_lodging_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_lodging_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](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 In two weeks [Mar 13 - Mar 15](https://www.expedia.ca/Hotel-Search?regionId=6341069&startDate=2026-03-13&endDate=2026-03-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Apr 24 - Apr 26](https://www.expedia.ca/Hotel-Search?regionId=6341069&startDate=2026-04-24&endDate=2026-04-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [May 22 - May 24](https://www.expedia.ca/Hotel-Search?regionId=6341069&startDate=2026-05-22&endDate=2026-05-24&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Jun 19 - Jun 21](https://www.expedia.ca/Hotel-Search?regionId=6341069&startDate=2026-06-19&endDate=2026-06-21&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) No exact matches found, but these alternatives could be just right ## Recommended hotels in Thimble Islands ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/10000/1500/1461/b5c018f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/10000/1500/1461/fcbc5aec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/1500/1461/d24fcc63.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, laptop workspace, iron/ironing board, free cribs/infant beds](https://images.trvl-media.com/lodging/1000000/10000/1500/1461/e0dc5e1c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Inn in The Centre [](https://www.expedia.ca/East-Haven-Hotels-Home2-Suites-By-Hilton-East-Haven-New-Haven.h1461.Hotel-Information) 9.6/10 Exceptional (491 reviews) "Good breakfast, great service. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Adrien CA $167 CA $192 total includes taxes & fees Mar 22 - Mar 23 [](https://www.expedia.ca/East-Haven-Hotels-Home2-Suites-By-Hilton-East-Haven-New-Haven.h1461.Hotel-Information) ![Free cribs/infant beds, rollaway beds, free WiFi, bed sheets](https://images.trvl-media.com/lodging/12000000/11960000/11951300/11951206/f9bec315.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free self parking](https://images.trvl-media.com/lodging/12000000/11960000/11951300/11951206/7836a152.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/12000000/11960000/11951300/11951206/f2520f08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free cribs/infant beds, rollaway beds, free WiFi, bed sheets](https://images.trvl-media.com/lodging/12000000/11960000/11951300/11951206/d1788901.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Motel in Clinton [](https://www.expedia.ca/Old-Saybrook-Hotels-Clinton-Motel.h11951206.Hotel-Information) 8.6/10 Excellent (302 reviews) "The room was comfortable and clean. A good value for the money." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michael CA $107 CA $123 total includes taxes & fees Feb 28 - Mar 1 [](https://www.expedia.ca/Old-Saybrook-Hotels-Clinton-Motel.h11951206.Hotel-Information) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/990000/983200/983128/dc9b088b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Combined shower/tub, hair dryer, towels, soap](https://images.trvl-media.com/lodging/1000000/990000/983200/983128/afd83ae8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/1000000/990000/983200/983128/174f7a84.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/990000/983200/983128/08241fb2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel in Guilford [](https://www.expedia.ca/Guilford-Hotels-Spark-By-Hilton-Guilford.h983128.Hotel-Information) 8.8/10 Excellent (99 reviews) "The front desk staff were excellent, clean and comfortable stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) JUstine CA $139 CA $160 total includes taxes & fees Mar 24 - Mar 25 [](https://www.expedia.ca/Guilford-Hotels-Spark-By-Hilton-Guilford.h983128.Hotel-Information) ![Bar (on property)](https://images.trvl-media.com/lodging/10000000/9680000/9679900/9679841/fc6ee41c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/10000000/9680000/9679900/9679841/0a9b90de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Villa, Multiple Beds, Ground Floor (by the Sea) | Beach/ocean view](https://images.trvl-media.com/lodging/10000000/9680000/9679900/9679841/25adc215.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 restaurants, breakfast, lunch, dinner served; Italian cuisine](https://images.trvl-media.com/lodging/10000000/9680000/9679900/9679841/c47845a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Resort in Westbrook Center [](https://www.expedia.ca/Old-Saybrook-Hotels-Waters-Edge-Resort-Spa.h9679841.Hotel-Information) 8.8/10 Excellent (1,009 reviews) "Great place!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Laura CA $267 CA $331 total includes taxes & fees Mar 1 - Mar 2 [](https://www.expedia.ca/Old-Saybrook-Hotels-Waters-Edge-Resort-Spa.h9679841.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/12200/12143/5cb2e3e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/1000000/20000/12200/12143/31bd2f7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/1000000/20000/12200/12143/a48f4b96.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/12200/12143/afdef753.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel in Saybrook Manor [](https://www.expedia.ca/Old-Saybrook-Hotels-Pier-Blue-Inn-Old-Saybrook-Essex.h12143.Hotel-Information) 8.0/10 Very good (1,000 reviews) "Room was clean and warm and the staff was very friendly " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Pattie [](https://www.expedia.ca/Old-Saybrook-Hotels-Pier-Blue-Inn-Old-Saybrook-Essex.h12143.Hotel-Information) ![Reception](https://images.trvl-media.com/lodging/1000000/10000/7600/7519/26c48632.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/10000/7600/7519/7e03ece1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/1000000/10000/7600/7519/ac5f55ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/10000/7600/7519/a5e9ab8b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel in North Haven [](https://www.expedia.ca/North-Haven-Hotels-Clarion-Inn.h7519.Hotel-Information) 7.6/10 Good (1,000 reviews) "Staff members were extremely helpful and kind from the people working the front desk to the house keeping people 5 stars to them " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) ray CA $135 CA $155 total includes taxes & fees Mar 1 - Mar 2 [](https://www.expedia.ca/North-Haven-Hotels-Clarion-Inn.h7519.Hotel-Information) ![Reception](https://images.trvl-media.com/lodging/1000000/880000/873200/873107/ee13375c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/880000/873200/873107/fd1eb309.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/1000000/880000/873200/873107/2572ad7e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/880000/873200/873107/aed7491f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel in Stratford [](https://www.expedia.ca/New-Haven-Hotels-Homewood-Suites-By-Hilton-Stratford.h873107.Hotel-Information) 8.8/10 Excellent (1,002 reviews) "Very friendly staff, clean hotel and very relaxing atmosphere." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Eugenia CA $151 CA $174 total includes taxes & fees Mar 21 - Mar 22 [](https://www.expedia.ca/New-Haven-Hotels-Homewood-Suites-By-Hilton-Stratford.h873107.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/130000/124400/124313/908bc53f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Queen Beds](https://images.trvl-media.com/lodging/1000000/130000/124400/124313/7fe4c218.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free buffet breakfast](https://images.trvl-media.com/lodging/1000000/130000/124400/124313/5c1dcb00.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/130000/124400/124313/a72b8077.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel in Branford [](https://www.expedia.ca/New-Haven-Hotels-Holiday-Inn-Express-Branford-New-Haven.h124313.Hotel-Information) 8.8/10 Excellent (1,000 reviews) "Staff very friendly, room very accomadating, clean and good breakfast" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Laurie CA $141 CA $162 total includes taxes & fees Mar 1 - Mar 2 [](https://www.expedia.ca/New-Haven-Hotels-Holiday-Inn-Express-Branford-New-Haven.h124313.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1400000/1400000/1399998/7368827e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/2000000/1400000/1400000/1399998/7fef8cbf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, coffee/tea maker](https://images.trvl-media.com/lodging/2000000/1400000/1400000/1399998/42c9a535.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1400000/1400000/1399998/cab0b22b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel in Guilford [](https://www.expedia.ca/New-Haven-Hotels-Tower-Inn-And-Suites-Of-Guilford-Madison.h1399998.Hotel-Information) 7.4/10 Good (238 reviews) "I really enjoy staying here. The family who runs this motel are so nice. I used to live in Guilford and moved out of state. I return to Conn frequently and always stay here. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Susan B CA $122 CA $141 total includes taxes & fees Mar 1 - Mar 2 [](https://www.expedia.ca/New-Haven-Hotels-Tower-Inn-And-Suites-Of-Guilford-Madison.h1399998.Hotel-Information) ![IPod dock, MP3 dock](https://images.trvl-media.com/lodging/2000000/1480000/1480000/1479959/497076d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Business centre](https://images.trvl-media.com/lodging/2000000/1480000/1480000/1479959/f543141b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 1 Bedroom, Private Bathroom](https://images.trvl-media.com/lodging/2000000/1480000/1480000/1479959/bf9d977d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior entrance](https://images.trvl-media.com/lodging/2000000/1480000/1480000/1479959/5ebf0e7e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bed & Breakfast in Westbrook Center [](https://www.expedia.ca/Westbrook-Hotels-Captain-Stannard-BB-Country-Inn.h1479959.Hotel-Information) 9.8/10 Exceptional (260 reviews) "The Inn and staff were warm and welcoming, the facility exceptionally clean. Breakfast exceeded my expectations for a continental breakfast! Would absolutely stay again! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lisa [](https://www.expedia.ca/Westbrook-Hotels-Captain-Stannard-BB-Country-Inn.h1479959.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/2000000/1570000/1562800/1562702/80833193.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, premium bedding, desk, laptop workspace](https://images.trvl-media.com/lodging/2000000/1570000/1562800/1562702/w3838h2557x0y0-f0aaceff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1570000/1562800/1562702/2a06d04a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/2000000/1570000/1562800/1562702/9d2203cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel in Milford [](https://www.expedia.ca/New-Haven-Hotels-Hyatt-Place-Milford-New-Haven.h1562702.Hotel-Information) 8.6/10 Excellent (1,253 reviews) "The staff was great, the room was very clean and the breakfast was very good. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Greg CA $141 CA $162 total includes taxes & fees Feb 28 - Mar 1 [](https://www.expedia.ca/New-Haven-Hotels-Hyatt-Place-Milford-New-Haven.h1562702.Hotel-Information) ![Individually decorated, individually furnished, desk, laptop workspace](https://images.trvl-media.com/lodging/2000000/1180000/1177400/1177328/0820f8f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/2000000/1180000/1177400/1177328/61b6e714.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1180000/1177400/1177328/db00678f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1180000/1177400/1177328/a27d78bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Motel in Old Saybrook [](https://www.expedia.ca/Old-Saybrook-Hotels-Econo-Lodge-Inn-Suites-Old-Saybrook-Westbrook.h1177328.Hotel-Information) 7.2/10 Good (467 reviews) "All good it met our expectations as a budget hotel. Large clean room bed was comfortable although the pillows were past it. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Hilary CA $92 CA $105 total includes taxes & fees Mar 5 - Mar 6 [](https://www.expedia.ca/Old-Saybrook-Hotels-Econo-Lodge-Inn-Suites-Old-Saybrook-Westbrook.h1177328.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1210000/1209400/1209378/1ec18076.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/2000000/1210000/1209400/1209378/c4093211.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 King Bed, Accessible (Roll In Shower)](https://images.trvl-media.com/lodging/2000000/1210000/1209400/1209378/5bf701c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1210000/1209400/1209378/f4c87c86.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel in Madison Center [](https://www.expedia.ca/Madison-Hotels-Madison-Beach-Hotel.h1209378.Hotel-Information) 9.4/10 Exceptional (346 reviews) "Staff and hotel are lovely " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Steven CA $335 CA $386 total includes taxes & fees Mar 5 - Mar 6 [](https://www.expedia.ca/Madison-Hotels-Madison-Beach-Hotel.h1209378.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/3000000/2480000/2473700/2473639/b8a2e8a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/3000000/2480000/2473700/2473639/5af2dc31.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/3000000/2480000/2473700/2473639/ba785aed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/3000000/2480000/2473700/2473639/268b5ae5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel in Milford [](https://www.expedia.ca/New-Haven-Hotels-Hilton-Garden-Inn-Milford.h2473639.Hotel-Information) 8.4/10 Very good (1,001 reviews) "staff was wonderful everything was spotless" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kelly CA $145 CA $166 total includes taxes & fees Mar 22 - Mar 23 [](https://www.expedia.ca/New-Haven-Hotels-Hilton-Garden-Inn-Milford.h2473639.Hotel-Information) ![Fireplace](https://images.trvl-media.com/lodging/36000000/35600000/35596400/35596310/62eddf34.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/36000000/35600000/35596400/35596310/cd675eea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/36000000/35600000/35596400/35596310/520263a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/36000000/35600000/35596400/35596310/82f07910.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bed & Breakfast in Westbrook Center [](https://www.expedia.ca/Old-Saybrook-Hotels-Westbrook-Inn-Bed-And-Breakfast.h35596310.Hotel-Information) 9.8/10 Exceptional (179 reviews) "Charming, beautiful inn; excellent food and service." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michael CA $282 CA $312 total includes taxes & fees Mar 10 - Mar 11 [](https://www.expedia.ca/Old-Saybrook-Hotels-Westbrook-Inn-Bed-And-Breakfast.h35596310.Hotel-Information) ![Free daily on-the-go breakfast](https://images.trvl-media.com/lodging/1000000/20000/13100/13007/6b5a7ce0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed](https://images.trvl-media.com/lodging/1000000/20000/13100/13007/8e287f35.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/20000/13100/13007/58bf94a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room (2 Double Queen Beds)](https://images.trvl-media.com/lodging/1000000/20000/13100/13007/d0ae630d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel in Milford [](https://www.expedia.ca/New-Haven-Hotels-Hampton-Inn-Milford.h13007.Hotel-Information) 7.8/10 Good (1,001 reviews) "good location " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michael CA $113 CA $130 total includes taxes & fees Mar 21 - Mar 22 [](https://www.expedia.ca/New-Haven-Hotels-Hampton-Inn-Milford.h13007.Hotel-Information) ![BBQ/picnic area](https://images.trvl-media.com/lodging/1000000/30000/23000/22935/1f39c492.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/30000/23000/22935/w1199h799x1y1-8d063a93.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, desk, blackout drapes, soundproofing](https://images.trvl-media.com/lodging/1000000/30000/23000/22935/w1199h799x1y1-45823d8d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Business centre](https://images.trvl-media.com/lodging/1000000/30000/23000/22935/w1199h799x1y1-35191aed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel in Wallingford [](https://www.expedia.ca/New-Haven-Hotels-Fairfield-Inn-By-Marriott-New-Haven-Wallingford.h22935.Hotel-Information) 8.8/10 Excellent (1,001 reviews) "Always stay here when visting family in CT." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) David CA $150 CA $172 total includes taxes & fees Mar 8 - Mar 9 [](https://www.expedia.ca/New-Haven-Hotels-Fairfield-Inn-By-Marriott-New-Haven-Wallingford.h22935.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/80000/79500/79426/d5c6959e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/80000/79500/79426/ee5d2f28.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, blackout drapes, iron/ironing board, free cribs/infant beds](https://images.trvl-media.com/lodging/1000000/80000/79500/79426/a463dd49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/80000/79500/79426/dcbfa3b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel in Orange [](https://www.expedia.ca/New-Haven-Hotels-Courtyard-By-Marriott-New-Haven-Orange-Milford.h79426.Hotel-Information) 8.4/10 Very good (1,007 reviews) "Staff, Room and Location " ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Umar CA $150 CA $172 total includes taxes & fees Mar 8 - Mar 9 [](https://www.expedia.ca/New-Haven-Hotels-Courtyard-By-Marriott-New-Haven-Orange-Milford.h79426.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1900000/1896600/1896545/6132396a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1900000/1896600/1896545/00c69c09.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1900000/1896600/1896545/d936e083.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1900000/1896600/1896545/c0034c2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Motel in Cheshire [](https://www.expedia.ca/New-Haven-Hotels-Cheshire-Welcome-Inn.h1896545.Hotel-Information) 8.4/10 Very good (786 reviews) "Great location, comfortable and clean" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) MARK CA $134 CA $154 total includes taxes & fees Mar 1 - Mar 2 [](https://www.expedia.ca/New-Haven-Hotels-Cheshire-Welcome-Inn.h1896545.Hotel-Information) ![Cooked-to-order breakfast for a fee](https://images.trvl-media.com/lodging/1000000/20000/19800/19783/1d0ef914.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast and dinner served, American cuisine](https://images.trvl-media.com/lodging/1000000/20000/19800/19783/d702eab6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/19800/19783/7edf3766.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/19800/19783/976415c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel in Wallingford [](https://www.expedia.ca/New-Haven-Hotels-Courtyard-New-Haven-Wallingford.h19783.Hotel-Information) 8.8/10 Excellent (790 reviews) "Clean room, friendly staff!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Julie CA $168 CA $193 total includes taxes & fees Mar 5 - Mar 6 [](https://www.expedia.ca/New-Haven-Hotels-Courtyard-New-Haven-Wallingford.h19783.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=2026-03-13&endDate=2026-03-14®ionId=6341069&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.ca/deals?rfrr=AA_SPRING_PROMO_6341069) ## Find vacation rentals that suit your style Aparthotels [](https://www.expedia.ca/Hotel-Search?destination=Thimble+Islands%2C+Connecticut%2C+United+States+of+America®ionId=6341069&latLong=41.248462%2C-72.754313&adults=2&startDate=2026-05-27&d1=2026-05-27&endDate=2026-05-30&d2=2026-05-30&lodging=APART_HOTEL) Cabins [](https://www.expedia.ca/Hotel-Search?destination=Thimble+Islands%2C+Connecticut%2C+United+States+of+America®ionId=6341069&latLong=41.248462%2C-72.754313&adults=2&startDate=2026-05-27&d1=2026-05-27&endDate=2026-05-30&d2=2026-05-30&lodging=CABIN) Cottages [](https://www.expedia.ca/Hotel-Search?destination=Thimble+Islands%2C+Connecticut%2C+United+States+of+America®ionId=6341069&latLong=41.248462%2C-72.754313&adults=2&startDate=2026-05-27&d1=2026-05-27&endDate=2026-05-30&d2=2026-05-30&lodging=COTTAGE) Apartments [](https://www.expedia.ca/Hotel-Search?destination=Thimble+Islands%2C+Connecticut%2C+United+States+of+America®ionId=6341069&latLong=41.248462%2C-72.754313&adults=2&startDate=2026-05-27&d1=2026-05-27&endDate=2026-05-30&d2=2026-05-30&lodging=APARTMENT) Condos [](https://www.expedia.ca/Hotel-Search?destination=Thimble+Islands%2C+Connecticut%2C+United+States+of+America®ionId=6341069&latLong=41.248462%2C-72.754313&adults=2&startDate=2026-05-27&d1=2026-05-27&endDate=2026-05-30&d2=2026-05-30&lodging=CONDO) Private vacation homes [](https://www.expedia.ca/Hotel-Search?destination=Thimble+Islands%2C+Connecticut%2C+United+States+of+America®ionId=6341069&latLong=41.248462%2C-72.754313&adults=2&startDate=2026-05-27&d1=2026-05-27&endDate=2026-05-30&d2=2026-05-30&lodging=VACATION_HOME) Houseboats [](https://www.expedia.ca/Hotel-Search?destination=Thimble+Islands%2C+Connecticut%2C+United+States+of+America®ionId=6341069&latLong=41.248462%2C-72.754313&adults=2&startDate=2026-05-27&d1=2026-05-27&endDate=2026-05-30&d2=2026-05-30&lodging=HOUSE_BOAT) ![](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%2FThimble-Islands-Condos.d6341069-aaCondos.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FThimble-Islands-Condos.d6341069-aaCondos.Travel-Guide-Accommodation) ## Top Thimble Islands Hotel Reviews ![Motel 6 Milford, CT](https://images.trvl-media.com/lodging/1000000/10000/300/291/4c692d71_y.jpg) ### Motel 6 Milford, CT 10/10 Excellent "Yes it was all good for me!" [](https://expedia.ca/New-Haven-Hotels-Motel-6-Milford.h291.Hotel-Information) ![Home2 Suites by Hilton East Haven New Haven](https://images.trvl-media.com/lodging/1000000/10000/1500/1461/b5c018f9_y.jpg) ### Home2 Suites by Hilton East Haven New Haven 10/10 Excellent "perfect room and ammenities. great place to stay. " [](https://expedia.ca/East-Haven-Hotels-Home2-Suites-By-Hilton-East-Haven-New-Haven.h1461.Hotel-Information) ![Water's Edge Resort & Spa](https://images.trvl-media.com/lodging/10000000/9680000/9679900/9679841/3723d6b0_y.jpg) ### Water's Edge Resort & Spa 10/10 Excellent "The staff throughout our stay was amazing. Our room was spotless and so comfortable. Beautiful view from the balcony. The spa was beautiful. We had relaxing massages. We ate in the main dining room. Our waiter was great and the food was amazing. We had so much fun using the jacuzzi and the pool which were very clean. So convenient having Starbucks in the hotel and a lovely gift shop. The valet staff were kind and helpful with our luggage. We will definitely stay here again and recommend this hotel for your stay. We went during the cold weather but would love to come back in the warmer weather." [](https://expedia.ca/Old-Saybrook-Hotels-Waters-Edge-Resort-Spa.h9679841.Hotel-Information) ![New Haven Hotel](https://images.trvl-media.com/lodging/1000000/40000/36800/36721/d665dc9c_y.jpg) ### New Haven Hotel 10/10 Excellent "The room was great, I love that it had a separate sink outside of the bathroom. Beds were comfortable and linens cozy." [](https://expedia.ca/New-Haven-Hotels-New-Haven-Hotel.h36721.Hotel-Information) ![Omni New Haven Hotel at Yale](https://images.trvl-media.com/lodging/1000000/50000/50000/49957/7466af25_y.jpg) ### Omni New Haven Hotel at Yale 10/10 Excellent "Comfortable, clean, quiet. Perfect atay" [](https://expedia.ca/New-Haven-Hotels-Omni-New-Haven-Hotel-At-Yale.h49957.Hotel-Information) ![Pier Blue Inn Old Saybrook - Essex](https://images.trvl-media.com/lodging/1000000/20000/12200/12143/a912ee6f_y.jpg) ### Pier Blue Inn Old Saybrook - Essex 10/10 Excellent "Very clean room. Staff was excellent. Very welcoming. Would and will stay there again, no question. " [](https://expedia.ca/Old-Saybrook-Hotels-Pier-Blue-Inn-Old-Saybrook-Essex.h12143.Hotel-Information) ![Hyatt Place Milford / New Haven](https://images.trvl-media.com/lodging/2000000/1570000/1562800/1562702/0336d577_y.jpg) ### Hyatt Place Milford / New Haven 10/10 Excellent "Excellent place, welcomed by desk staff, smooth and fast check in. Room clean and spacious." [](https://expedia.ca/New-Haven-Hotels-Hyatt-Place-Milford-New-Haven.h1562702.Hotel-Information) ![Courtyard by Marriott New Haven Orange-Milford](https://images.trvl-media.com/lodging/1000000/80000/79500/79426/bdad3f31_y.jpg) ### Courtyard by Marriott New Haven Orange-Milford 10/10 Excellent "everything was great!" [](https://expedia.ca/New-Haven-Hotels-Courtyard-By-Marriott-New-Haven-Orange-Milford.h79426.Hotel-Information) ![Homewood Suites by Hilton Orange New Haven](https://images.trvl-media.com/lodging/39000000/38980000/38980000/38979983/cf46bed4_y.jpg) ### Homewood Suites by Hilton Orange New Haven 10/10 Excellent "The room was clean, the pool and hot tub are open and maintained. Staff were kind and helpful. The breakfast was what you would expect for a hotel breakfast. We arrived at 4 and our room wasn't ready, but did not take log and getting a late checkout was easy. I would recommend staying here." [](https://expedia.ca/New-Haven-Hotels-Homewood-Suites-By-Hilton-Orange-New-Haven.h38979983.Hotel-Information) ## Find out more about Thimble Islands ## Thimble Islands Condo Rentals information | Number of reviews | 13,972 | | ----------------- | ---------------- | | Accommodation | 11 Condo Rentals | | Lowest Price | CA $105 | | Highest Price | CA $386 | ## Frequently asked questions ### Why book your condo in Thimble Islands with Expedia? ### How can I find cheap condos in Thimble Islands? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - More ways to book - [4 Star Hotels in Guilford ](https://www.expedia.ca/4Star-Guilford-Hotels.s40-0-d183062.Travel-Guide-Filter-Hotels) - [Hotels near Bill Miller’s Castle ](https://www.expedia.ca/Bill-Millers-Castle-Hotels.0-l553248621563220905-0.Travel-Guide-Filter-Hotels) - [Aparthotels in Branford ](https://www.expedia.ca/Branford-Apart-Hotels.d6243-aaApartHotels.Travel-Guide-Accommodation) - 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