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 $128 ![](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 16 - Oct 17](https://www.expedia.ca/Hotel-Search?regionId=641785043103088640&startDate=2025-10-16&endDate=2025-10-17&adults=2&propertyStyle=BOUTIQUE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 17 - Oct 18](https://www.expedia.ca/Hotel-Search?regionId=641785043103088640&startDate=2025-10-17&endDate=2025-10-18&adults=2&propertyStyle=BOUTIQUE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=641785043103088640&startDate=2025-10-17&endDate=2025-10-19&adults=2&propertyStyle=BOUTIQUE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next 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) ## 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=2025-10-30&endDate=2025-10-31®ionId=641785043103088640&adults=2) ## Recommended hotels in Wooster Square ![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/92000000/91260000/91256000/91255933/6936fc87.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/92000000/91260000/91256000/91255933/9b91f981.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!!" CA $152 CA $636 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/New-Haven-Hotels-Modern-Spacious-Studio-In-Wooster-Squre.h91255933.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/94000000/93400000/93397900/93397837/480cd07c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, books](https://images.trvl-media.com/lodging/94000000/93400000/93397900/93397837/4f9a29c4.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) ![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 " CA $146 CA $288 total includes taxes & fees Oct 23 - Oct 24 [](https://www.expedia.ca/New-Haven-Hotels-The-Matisse-At-Wooster-Square-Yale-Parking.h93397837.Hotel-Information) ![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/112000000/111800000/111794700/111794609/f05cc6aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/112000000/111800000/111794700/111794609/07642cd1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/112000000/111800000/111794700/111794609/a8db9992.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/112000000/111800000/111794700/111794609/01e9484f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming Wooster Square flat - Walk to Pizza & Yale! - FREE Parking & Laundry Mill River CA $226 CA $617 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/New-Haven-Hotels-Charming-3-Bed-Wooster-Square-Apartment-Near-Yale-In-New-Haven.h111794609.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) ![Exterior](https://images.trvl-media.com/lodging/120000000/119310000/119305300/119305255/7ddae396.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) ![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! " CA $169 CA $471 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/New-Haven-Hotels-A-Bricks-Throw-Away-To-Sallys-Apizza.h119305255.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) ![1 bedroom, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/68000000/67640000/67632200/67632125/f177dc57.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) ![Interior](https://images.trvl-media.com/lodging/68000000/67640000/67632200/67632125/9f99a45d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Unit 101 · RENOVATED, 1 mile from YALE! Mill River CA $173 CA $316 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) ![TV, fireplace, books](https://images.trvl-media.com/lodging/94000000/93290000/93288200/93288128/6542a142.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) ![Interior](https://images.trvl-media.com/lodging/94000000/93290000/93288200/93288128/eba8fa92.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." CA $222 CA $521 total includes taxes & fees Oct 21 - Oct 22 [](https://www.expedia.ca/New-Haven-Hotels-The-Brick-Wooster-Square-Yale-Skyline-Deck.h93288128.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) ![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) ![Front of property](https://images.trvl-media.com/lodging/1000000/990000/983200/983128/735ceae9.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) ### Spark by Hilton Guilford Guilford 8.6/10 Excellent (43) "Good clean property with great staff " CA $159 CA $183 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Guilford-Hotels-Spark-By-Hilton-Guilford.h983128.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) ![Fridge, coffee/tea maker](https://images.trvl-media.com/lodging/1000000/40000/34300/34227/8d58fa7c.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) ![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) ### Courtyard by Marriott Waterbury Downtown Waterbury 8.4/10 Very good (1021) "Wonderful stay " CA $111 CA $128 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/New-Haven-Hotels-Courtyard-By-Marriott-Waterbury-Downtown.h34227.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 sitting area](https://images.trvl-media.com/lodging/1000000/40000/36800/36721/92e73287.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) ![Reception](https://images.trvl-media.com/lodging/1000000/40000/36800/36721/cefd8f92.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### New Haven Hotel Downtown New Haven 9.0/10 Wonderful (1842) "The hotel was very nice. The room was clean and the staff was very friendly. " 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) ![Exterior](https://images.trvl-media.com/lodging/72000000/71430000/71427300/71427300/1699c03c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/72000000/71430000/71427300/71427300/2ee9a3b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed, Accessible, Bathtub](https://images.trvl-media.com/lodging/72000000/71430000/71427300/71427300/fdb0e84f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/72000000/71430000/71427300/71427300/c8eabbef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel Marcel New Haven, Tapestry Collection By Hilton Long Wharf 9.4/10 Exceptional (812) "The hotel and staff were fabulous." CA $195 CA $224 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/New-Haven-Hotels-Hotel-Marcel-New-Haven.h71427300.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=2025-10-30&endDate=2025-10-31®ionId=641785043103088640&adults=2&specialized_stays_group_explore=boutique_property&sort=RECOMMENDED&openPlayBack=true) ## Top Wooster Square Hotel Reviews ![New Haven Hotel](//images.trvl-media.com/lodging/1000000/40000/36800/36721/dd69cbb4_y.jpg) ### New Haven Hotel 10/10 Excellent "We stayed one night. The staff was welcoming, the room clean and quiet, the bed very comfortable. " [](https://expedia.ca/New-Haven-Hotels-New-Haven-Hotel.h36721.Hotel-Information) ![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 "Yes" [](https://expedia.ca/New-Haven-Hotels-Hyatt-Place-Milford-New-Haven.h1562702.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. Some other things you might want to enjoy include Peabody Museum of Natural History, Shoreline Trolley Museum, and Toyota Oakdale Theatre. ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Other - More ways to book - [4 Star Hotels in Quinnipiac Meadows](https://www.expedia.ca/4Star-Quinnipiac-Meadows-New-Haven-Hotels.s40-n899951259073933312-0.Travel-Guide-Filter-Hotels) - [Hotels near Albertus Magnus College](https://www.expedia.ca/Albertus-Magnus-College-Hotels.0-l6176929-0.Travel-Guide-Filter-Hotels) - [Allingtown Hotels](https://www.expedia.ca/Allingtown-Hotels.d3000420703.Travel-Guide-Hotels) - [Beaver Hills Hotels](https://www.expedia.ca/Beaver-Hills-New-Haven-Hotels.0-n553248635976476440-0.Travel-Guide-Filter-Hotels) - [Hotels with Early Check-in in Connecticut](https://www.expedia.ca/Destinations-In-Connecticut-Hotel-With-Early-Check-In.0-0-d208-thotelwithearlycheckin.Hotel-Filter-Destinations) - [Hotels with a Pool in Connecticut](https://www.expedia.ca/Destinations-In-Connecticut-Hotel-With-Pool.0-0-d208-tHotelwithPool.Hotel-Filter-Destinations) - 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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)