Title: Wellesley Guest Houses from CA $219 | Expedia.ca [Wellesley Travel Guide](https://expedia.ca/Wellesley.dx7665)[Hotels in Wellesley](https://expedia.ca/Wellesley-Hotels.d7665.Travel-Guide-Hotels)[Vacation Rentals in Wellesley](https://expedia.ca/Wellesley-Vacation-Rentals.d7665.Travel-Guide-VacationRentals)[Flights to Wellesley](https://expedia.ca/Cheap-Flights-To-Wellesley.d7665.Travel-Guide-Flights)[Wellesley Car Rentals](https://expedia.ca/Car-Rentals-In-Wellesley.d7665.Car-Rental-Guide)[Wellesley Vacation Packages](https://expedia.ca/Wellesley.d7665.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/2/a34447f2f6d32261a17bf6777ddc3e35.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Fun Travelog # Search Guest Houses in Wellesley from CA $219 ![](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 Next weekend [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=7665&startDate=2025-10-31&endDate=2025-11-02&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=7665&startDate=2025-11-07&endDate=2025-11-09&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=7665&startDate=2025-11-21&endDate=2025-11-23&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=7665&startDate=2025-12-19&endDate=2025-12-21&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Wellesley Guest Houses ![Exterior](https://images.trvl-media.com/lodging/2000000/1150000/1145300/1145259/31868feb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Economy Double Room, Ensuite](https://images.trvl-media.com/lodging/2000000/1150000/1145300/1145259/f81a74b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1150000/1145300/1145259/4aea60d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/2000000/1150000/1145300/1145259/e425e9d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Oasis Guest House Fenway–Kenmore 9.6/10 Exceptional (1336) "Would stay again " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jennifer CA $221 CA $254 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Boston-Hotels-Oasis-Guest-House.h1145259.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/6000000/5230000/5227600/5227514/48469faa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/6000000/5230000/5227600/5227514/876e12fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/6000000/5230000/5227600/5227514/c8acdf30.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hallway](https://images.trvl-media.com/lodging/6000000/5230000/5227600/5227514/2e412f68.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Coolidge Corner Guest House Coolidge Corner South Side 8.2/10 Very good (623) "Very pleasant, comfortable stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Valerie CA $224 CA $250 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Boston-Hotels-Coolidge-Corner-Guest-House.h5227514.Hotel-Information) ![Property entrance](https://images.trvl-media.com/lodging/2000000/1490000/1482500/1482493/0af3b824.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Studio, 1 King Bed with Sofa bed, Kitchen](https://images.trvl-media.com/lodging/2000000/1490000/1482500/1482493/67115820.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Studio Suite, 1 Queen Bed with Sofa bed, Kitchen](https://images.trvl-media.com/lodging/2000000/1490000/1482500/1482493/e742e199.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/2000000/1490000/1482500/1482493/ac01edf4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Copley House Back Bay 9.0/10 Wonderful (1865) "It was a great place to stay,,,we have stayed there 4 times in the past 2 months..." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kathleen CA $278 CA $319 total includes taxes & fees Oct 31 - Nov 1 [](https://www.expedia.ca/Boston-Hotels-Copley-House.h1482493.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/2000000/1180000/1170200/1170159/d574c037.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/2000000/1180000/1170200/1170159/60b0244b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, premium bedding, Tempur-Pedic beds, individually decorated](https://images.trvl-media.com/lodging/2000000/1180000/1170200/1170159/ce84b5b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/2000000/1180000/1170200/1170159/9d20e578.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Inn on the Horse Farm Sudbury 8.0/10 Very good (261) "Great area, historic. Near restaurants. Able to wander the property. Nice to relax before our journey home." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) David CA $222 CA $249 total includes taxes & fees Oct 31 - Nov 1 [](https://www.expedia.ca/Boston-Hotels-The-Inn-On-The-Horse-Farm.h1170159.Hotel-Information) ![Room](https://images.trvl-media.com/lodging/1000000/900000/893000/892946/4b98a457.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/900000/893000/892946/c04ca267.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/900000/893000/892946/51517f14.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room](https://images.trvl-media.com/lodging/1000000/900000/893000/892946/80cba54f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beacon Inn 1750 Cleveland Circle 7.4/10 Good (747) "Excellent for the price and location." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) John CA $196 CA $219 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Boston-Hotels-Beacon-Inn-1750.h892946.Hotel-Information) ![Standard Double Room, 1 Double Bed, Shared Bathroom | Private kitchen](https://images.trvl-media.com/lodging/22000000/21420000/21410900/21410883/be00b22a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/22000000/21420000/21410900/21410883/f80ad6a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Double Room, 1 Double Bed, Shared Bathroom](https://images.trvl-media.com/lodging/22000000/21420000/21410900/21410883/713d9857.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bicycling](https://images.trvl-media.com/lodging/22000000/21420000/21410900/21410883/00fcaaee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Tranquil House in Cambridge Strawberry Hill 8.8/10 Excellent (157) "Is very quiet and very clean " ![Mexico](https://a.travel-assets.com/egds/marks/flags/mx.svg) ALEJANDRO CA $208 CA $238 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Boston-Hotels-Kitty-House-Near-Harvard-Square.h21410883.Hotel-Information) ![King Room @ 1087 Beacon St. ](https://images.trvl-media.com/lodging/1000000/890000/889800/889743/ac883cf0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/890000/889800/889743/c580a535.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Double Room with One Double Bed and Private Detached Bath @ 1087 Beacon St. | Bathroom](https://images.trvl-media.com/lodging/1000000/890000/889800/889743/880d6c4e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/890000/889800/889743/c00ee678.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beacon Inn 1087 Longwood 8.0/10 Very good (768) "Great location. Not worth the price though." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Charles CA $222 CA $248 total includes taxes & fees Oct 30 - Oct 31 [](https://www.expedia.ca/Boston-Hotels-Beacon-Inn-1087.h889743.Hotel-Information) ![1 bedroom, premium bedding, down comforters, minibar](https://images.trvl-media.com/lodging/2000000/1150000/1145300/1145270/17519ab4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Suite, Private Bathroom](https://images.trvl-media.com/lodging/2000000/1150000/1145300/1145270/44118475.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/2000000/1150000/1145300/1145270/baa5f11b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/2000000/1150000/1145300/1145270/7eef0e7d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Clarendon Square South End 9.2/10 Wonderful (247) "In a word: charming" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) David [](https://www.expedia.ca/Boston-Hotels-Clarendon-Square-Bed-Breakfast.h1145270.Hotel-Information) ![Fridge, microwave, oven, dishwasher](https://images.trvl-media.com/lodging/115000000/114180000/114173800/114173750/a60c0158.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/115000000/114180000/114173800/114173750/4d62b58c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Combined shower/tub, soap, toilet paper](https://images.trvl-media.com/lodging/115000000/114180000/114173800/114173750/4c7c5b5f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/115000000/114180000/114173800/114173750/35aa1738.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 184 Heath St Jamaica Plain 2.8/10 (30) "Someone at the property had to let me in and text the property manager to send me my check in information. The front door barely closes, the pillows thinner than plywood and feel about as comfortable. Feels like a halfway house. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Drayton CA $119 CA $222 total includes taxes & fees Oct 23 - Oct 24 [](https://www.expedia.ca/Boston-Hotels-184-Heath-St.h114173750.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/109000000/108440000/108435200/108435179/d763a41f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/109000000/108440000/108435200/108435179/e08c4325.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Family Room](https://images.trvl-media.com/lodging/109000000/108440000/108435200/108435179/59ef104a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Basic Room | Private kitchen](https://images.trvl-media.com/lodging/109000000/108440000/108435200/108435179/f937a2cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### ESJACPE GUEST HOUSE Jamaica Plain 2.8/10 (26) "No Toilet paper or towels or soap. Just an old house in Boston that rents rooms. THATS IT. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tim CA $189 CA $345 total includes taxes & fees Oct 23 - Oct 24 [](https://www.expedia.ca/Boston-Hotels-ESJACPE-GUEST-HOUSE.h108435179.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=2025-11-05&endDate=2025-11-06®ionId=7665&adults=2&lodging=GUEST_HOUSE&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%2FWellesley-Guest-Houses.d7665-aaGuestHouses.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWellesley-Guest-Houses.d7665-aaGuestHouses.Travel-Guide-Accommodation) ## Top Wellesley Hotel Reviews ![Hampton Inn Boston - Logan Airport](//images.trvl-media.com/lodging/1000000/580000/578500/578419/w3839h2488x0y0-d5429574_y.jpg) ### Hampton Inn Boston - Logan Airport 10/10 Excellent "The staff were able to drop off an item i left behind all the way to the airport as i needed the item for my little girl. They went above and beyond for me and i am forever grateful. " [](https://expedia.ca/Boston-Hotels-Hampton-Inn-Boston-Logan-Airport.h578419.Hotel-Information) ![The Godfrey Hotel Boston](//images.trvl-media.com/lodging/11000000/10120000/10118700/10118614/e4d256d2_y.jpg) ### The Godfrey Hotel Boston 10/10 Excellent "Everyone was very nice" [](https://expedia.ca/Boston-Hotels-The-Godfrey-Hotel-Boston.h10118614.Hotel-Information) ![Hilton Boston Logan Airport](//images.trvl-media.com/lodging/1000000/290000/281600/281536/23c65d09_y.jpg) ### Hilton Boston Logan Airport 10/10 Excellent "Love staying here before an early morning flight. Quick, easy and stress free walk to the airport through the sky bridge " [](https://expedia.ca/Boston-Hotels-Hilton-Boston-Logan-Airport.h281536.Hotel-Information) ![The Langham, Boston](//images.trvl-media.com/lodging/1000000/10000/2600/2558/9a3ebe8a_y.jpg) ### The Langham, Boston 10/10 Excellent "I would never stay any where else. Absolutely amazing. " [](https://expedia.ca/Boston-Hotels-The-Langham.h2558.Hotel-Information) ![citizenM Boston Back Bay](//images.trvl-media.com/lodging/97000000/97000000/96998900/96998829/90056141_y.jpg) ### citizenM Boston Back Bay 10/10 Excellent "A cruise ship sized room with universal remote capabilities ..It's not fancy but it's unique and extremely easy to adjust to. My favorite part is mood lighting and soundproof feel topped with electric dark and day window screen technology and quirky signage. This location is one of the best for back bay access . " [](https://expedia.ca/Boston-Hotels-CitizenM-Boston-Back-Bay.h96998829.Hotel-Information) ![The Dagny Boston](//images.trvl-media.com/lodging/1000000/160000/151300/151201/4c15d693_y.jpg) ### The Dagny Boston 10/10 Excellent "Great staff, friendly, helpful. Nice cafe, beautiful, comfortable room. Clean rooms, lobby, elevators. " [](https://expedia.ca/Boston-Hotels-Hilton-Boston-DowntownFaneuil-Hall.h151201.Hotel-Information) ![Copley Square Hotel, a FOUND Hotel](//images.trvl-media.com/lodging/1000000/20000/16100/16067/dbccf1fb_y.jpg) ### Copley Square Hotel, a FOUND Hotel 10/10 Excellent "This is a great hotel for solo travelers because they offer a smaller size room with a full-sized bed for a reduced rate. Rooms are clean/modern and have mini-fridges (w/ tiny freezer) and free bottled water. There is a guest kitchen on the first floor with vending machines and free 24/7 coffee/tea. Also on the first floor is a small gym with a treadmill, elliptical, and weights. Service is impeccably professional and the property is very quiet, despite being steps away from the Prudential Center Mall, Copley Plaza, and Boylston/Newbury Streets. This hotel has become my new go-to when I'm coming into the city for events. " [](https://expedia.ca/Boston-Hotels-Copley-Square-Hotel.h16067.Hotel-Information) ![citizenM Boston North Station](//images.trvl-media.com/lodging/34000000/33880000/33870600/33870542/0eda38d5_y.jpg) ### citizenM Boston North Station 10/10 Excellent "Great hotel. Location is perfect! Staff were a little odd, very young, they didn’t have the best hospitality." [](https://expedia.ca/Boston-Hotels-CitizenM-Boston-North-Station.h33870542.Hotel-Information) ![Encore Boston Harbor](//images.trvl-media.com/lodging/38000000/37060000/37057200/37057112/9dbd3cd5_y.jpg) ### Encore Boston Harbor 10/10 Excellent "Modern, spacious and immaculate room. View on the harbor was beautiful. Rare Steakhouse was wonderful. Meat was excellent and so was the service. " [](https://expedia.ca/Boston-Hotels-Encore-Boston-Harbor.h37057112.Hotel-Information) ## Find out more about Wellesley ## Wellesley Guest Houses information | Number of reviews | 5,635 | | --- | --- | | Accommodation | 16 Guest Houses | | Lowest Price | CA $219 | | Highest Price | CA $345 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - More ways to book - [4 Star Hotels in Newton Upper Falls](https://www.expedia.ca/4Star-Newton-Upper-Falls-Boston-Hotels.s40-n138330-0.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Auburndale](https://www.expedia.ca/Auburndale-Boston-Hotels-Cheap-Hotels.0-n75534-0-tCheapHotels.Travel-Guide-Filter-Hotels) - [Hotels with Hot Tubs in Auburndale](https://www.expedia.ca/Auburndale-Boston-Hotels-Hotels-With-Hot-Tubs.0-n75534-0-tHotelsWithHotTubs.Travel-Guide-Filter-Hotels) - [Spa Hotels in Auburndale](https://www.expedia.ca/Auburndale-Boston-Hotels-Spa-Hotel.0-n75534-0-tSpaHotel.Travel-Guide-Filter-Hotels) - [Auburndale Hotels](https://www.expedia.ca/Auburndale-Boston-Hotels.0-n75534-0.Travel-Guide-Filter-Hotels) - 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