Title: Book the Best BOUTIQUE Hotels in Wooster Square in 2025 | Expedia.ca [Vacation Rentals in New Haven](https://expedia.ca/New-Haven-Vacation-Rentals.d180036.Travel-Guide-VacationRentals)[Flights to New Haven](https://expedia.ca/Cheap-Flights-To-New-Haven.d180036.Travel-Guide-Flights)[Things to do in New Haven](https://expedia.ca/Things-To-Do-In-New-Haven.d180036.Travel-Guide-Activities)[Wooster Square Car Rentals](https://expedia.ca/Car-Rentals-In-Wooster-Square.d641785043103088640.Car-Rental-Guide)[Wooster Square Vacations](https://expedia.ca/Wooster-Square.d641785043103088640.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/2/415484820687fbf8e195b93597fcdbd2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Anthony Salonga # Find Boutique Hotels in Wooster Square, CT from CA $127 ![](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 Wooster Square Boutique Hotels Tonight [Oct 20 - Oct 21](https://www.expedia.ca/Hotel-Search?regionId=641785043103088640&startDate=2025-10-20&endDate=2025-10-21&adults=2&propertyStyle=BOUTIQUE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 21 - Oct 22](https://www.expedia.ca/Hotel-Search?regionId=641785043103088640&startDate=2025-10-21&endDate=2025-10-22&adults=2&propertyStyle=BOUTIQUE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=641785043103088640&startDate=2025-10-24&endDate=2025-10-26&adults=2&propertyStyle=BOUTIQUE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=641785043103088640&startDate=2025-10-31&endDate=2025-11-02&adults=2&propertyStyle=BOUTIQUE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Wooster Square Boutique Hotels We don't have any properties that match your exact search [See all properties in Wooster Square](https://expedia.ca/Hotel-Search?startDate=2025-11-03&endDate=2025-11-04®ionId=641785043103088640&adults=2) ## Recommended hotels in Wooster Square ![Exterior detail](https://images.trvl-media.com/lodging/94000000/93400000/93397900/93397837/480cd07c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/94000000/93400000/93397900/93397837/0ecafe43.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, books](https://images.trvl-media.com/lodging/94000000/93400000/93397900/93397837/7bc81df3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/94000000/93400000/93397900/93397837/77f9aeff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Matisse at Wooster Square | Yale | Parking Mill River 10/10 Exceptional (2) "Exactly as advertised great place for 2. Excellent communication with owners and great time would highly recommend " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sid B. CA $150 CA $290 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/New-Haven-Hotels-The-Matisse-At-Wooster-Square-Yale-Parking.h93397837.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119310000/119305300/119305255/d3377c49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/120000000/119310000/119305300/119305255/26e68097.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/120000000/119310000/119305300/119305255/7ddae396.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119310000/119305300/119305255/6f7bb739.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### A brick's throw away to Sally's Apizza! Mill River 10/10 Exceptional (2) "The perfect place for visiting my Yale student! The space was comfortable for her to come visit, far enough from campus for a beak but close enough to get to class. Loved the full kitchen to provide her a home cooked meal and access to the washer and dryer so we could do her laundry. We can’t wait to stay again! I highly recommend both coffee locations and the liquor store in the neighborhood. And of course Sally’s! The host was amazing and communicated nearly immediately when I had questions! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Brandi J. CA $246 CA $560 total includes taxes & fees Oct 21 - Oct 22 [](https://www.expedia.ca/New-Haven-Hotels-A-Bricks-Throw-Away-To-Sallys-Apizza.h119305255.Hotel-Information) ![Private kitchen](https://images.trvl-media.com/lodging/112000000/111820000/111815700/111815688/cb885f74.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/112000000/111820000/111815700/111815688/9e704937.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/112000000/111820000/111815700/111815688/f4ded058.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/112000000/111820000/111815700/111815688/126a3ad2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wooster Gem - Walk to Pizza & Yale! - FREE Parking and Laundry Mill River 10/10 Exceptional (1) "The host was very responsive. I would recommend Vrbo as well as this host for future stays." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Larmeka A. CA $212 CA $594 total includes taxes & fees Nov 20 - Nov 21 [](https://www.expedia.ca/New-Haven-Hotels-Stylish-2-Bedroom-Apartment-In-Lovely-Wooster-Square-New-Haven-Near-Yale.h111815688.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/92000000/91260000/91256000/91255933/22f0e02c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/92000000/91260000/91256000/91255933/fd64e636.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/92000000/91260000/91256000/91255933/04737906.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/92000000/91260000/91256000/91255933/6936fc87.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Escape - Wooster Square Mill River 8.2/10 Very good (10) "Great experience at this property! Host was in contact with me throughout my stay, which was a nice surprise! It’s a cute studio, with AC and parking which was perfect! Definitely would stay here again when visiting New Haven!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Katie R. CA $151 CA $624 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/New-Haven-Hotels-Modern-Spacious-Studio-In-Wooster-Squre.h91255933.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/68000000/67640000/67632300/67632208/ceea1768.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/68000000/67640000/67632300/67632208/0caf21d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/68000000/67640000/67632300/67632208/86d55382.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/68000000/67640000/67632300/67632208/5917a78b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Unit 102 · NEAR YALE AND DOWNTOWN NEWLY RENOVATED Mill River CA $187 CA $331 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/New-Haven-Hotels-Unit-102-NEAR-YALE-AND-DOWNTOWN-NEWLY-RENOVATED.h67632208.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/68000000/67640000/67632200/67632125/a882153d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/68000000/67640000/67632200/67632125/9f99a45d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/68000000/67640000/67632200/67632125/6e6f7cf4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/68000000/67640000/67632200/67632125/fd0e46a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Unit 101 · RENOVATED, 1 mile from YALE! Mill River CA $173 CA $321 total includes taxes & fees Oct 23 - Oct 24 [](https://www.expedia.ca/New-Haven-Hotels-Unit-101-RENOVATED.h67632125.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/94000000/93290000/93288200/93288128/89745380.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/94000000/93290000/93288200/93288128/72517dae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/94000000/93290000/93288200/93288128/eba8fa92.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/94000000/93290000/93288200/93288128/87761395.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Brick Wooster Square | Yale | Skyline Deck Mill River 8.6/10 Excellent (8) "Nice unit in a good, walkable location. Comfortable beds, nice bathrooms and spacious." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) George S. CA $191 CA $492 total includes taxes & fees Nov 18 - Nov 19 [](https://www.expedia.ca/New-Haven-Hotels-The-Brick-Wooster-Square-Yale-Skyline-Deck.h93288128.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/40000/34300/34227/c0e669e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/1000000/40000/34300/34227/e1028a1a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/1000000/40000/34300/34227/24fc1ee6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/1000000/40000/34300/34227/db5c54a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Courtyard by Marriott Waterbury Downtown Waterbury 8.4/10 Very good (1026) "Wonderful stay " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Hyana CA $111 CA $127 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/New-Haven-Hotels-Courtyard-By-Marriott-Waterbury-Downtown.h34227.Hotel-Information) ![Reception](https://images.trvl-media.com/lodging/1000000/990000/983200/983128/08241fb2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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) ![Room, 2 Queen Beds](https://images.trvl-media.com/lodging/1000000/990000/983200/983128/bc78fd2a.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) ### Spark by Hilton Guilford Guilford 8.6/10 Excellent (44) "Good clean property with great staff " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) David CA $160 CA $184 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Guilford-Hotels-Spark-By-Hilton-Guilford.h983128.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/1000000/40000/36800/36721/dd69cbb4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/40000/36800/36721/a44234e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/40000/36800/36721/a42cca00.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/40000/36800/36721/92e73287.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### New Haven Hotel Downtown New Haven 9.0/10 Wonderful (1852) "The hotel was very nice. The room was clean and the staff was very friendly. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Vanessa L CA $160 CA $184 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/New-Haven-Hotels-New-Haven-Hotel.h36721.Hotel-Information) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply. [View all properties](https://expedia.ca/Hotel-Search?startDate=2025-11-03&endDate=2025-11-04®ionId=641785043103088640&adults=2&specialized_stays_group_explore=boutique_property&sort=RECOMMENDED&openPlayBack=true) ## Top Wooster Square Hotel Reviews ![Hyatt Place Milford / New Haven](//images.trvl-media.com/lodging/2000000/1570000/1562800/1562702/0336d577_y.jpg) ### Hyatt Place Milford / New Haven 10/10 Excellent "Rooms look old some of the furniture looks well used" [](https://expedia.ca/New-Haven-Hotels-Hyatt-Place-Milford-New-Haven.h1562702.Hotel-Information) ![New Haven Hotel](//images.trvl-media.com/lodging/1000000/40000/36800/36721/dd69cbb4_y.jpg) ### New Haven Hotel 10/10 Excellent "Great location and the staff was warm and friendly. Stay here. " [](https://expedia.ca/New-Haven-Hotels-New-Haven-Hotel.h36721.Hotel-Information) ## Frequently asked questions ### What's there to see and do in Wooster Square? > Once you've decided where you'd like to stay, consider what to do for fun during your trip. Activities and attractions to experience around Wooster Square include Wooster Square, New Haven City Hall, and Shubert Theater. 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[Visit City Point](https://www.expedia.ca/New-Haven-City-Point.dx6349499) - [Visit Dixwell](https://www.expedia.ca/New-Haven-Dixwell.dx899950114098167808) - [Visit Fair Haven](https://www.expedia.ca/New-Haven-Fair-Haven.dx6349505) - [New Haven Vacations](https://www.expedia.ca/New-Haven.d180036.Destination-Travel-Guides) - [Visit New Haven](https://www.expedia.ca/New-Haven.dx180036) - [Sterling Memorial Library at Yale University](https://www.expedia.ca/Sterling-Memorial-Library-At-Yale-University-Downtown-New-Haven.d6071481.Vacation-Attraction) - [Yale University Art Gallery](https://www.expedia.ca/Yale-University-Art-Gallery-Downtown-New-Haven.d6071487.Vacation-Attraction) - [Yale University](https://www.expedia.ca/Yale-University-Downtown-New-Haven.d502016.Vacation-Attraction) - [Car rental New Haven](https://www.expedia.ca/Car-Rentals-In-New-Haven.d180036.Car-Rental-Guide) - [Car rentals near Yale University](https://www.expedia.ca/Car-Rentals-In-Yale-University.d502016.Car-Rental-Guide) - [Things to do in New Haven](https://www.expedia.ca/Things-To-Do-In-New-Haven.d180036.Travel-Guide-Activities) - [Book Hotels in Wooster Square on Expedia.com](https://www.expedia.com/Wooster-Square-New-Haven-Hotels-Boutique-Hotel.0-n641785043103088640-0-tBoutiqueHotel.Travel-Guide-Filter-Hotels)