Title: Wellesley, MA Guest Houses from $99 | Expedia.com [Wellesley Travel Guide](https://expedia.com/Wellesley.dx7665)[Hotels in Wellesley](https://expedia.com/Wellesley-Hotels.d7665.Travel-Guide-Hotels)[Vacation Rentals in Wellesley](https://expedia.com/Wellesley-Vacation-Rentals.d7665.Travel-Guide-VacationRentals)[Flights to Wellesley](https://expedia.com/Cheap-Flights-To-Wellesley.d7665.Travel-Guide-Flights)[Car Rentals in Wellesley](https://expedia.com/Car-Rentals-In-Wellesley.d7665.Car-Rental-Guide)[Wellesley Vacation Packages](https://expedia.com/Wellesley.d7665.Destination-Travel-Guides) ![Lodging Image](https://a.travel-assets.com/travel-assets-manager/bex-affinities/lodging.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://a.travel-assets.com/travel-assets-manager/bex-affinities/lodging.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light_bundle_and_save.svg) ### Bundle & Save Get more, spend less whenever you see Bundle & Save deals - ![](https://a.travel-assets.com/travel-assets-manager/pictograms-expedia/light__onekey.svg) ### OneKeyCash Earn OneKeyCash on all your eligible bookings - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light_ftc.svg) ### Upfront pricing We are not like the others - we include taxes and fees ## Check prices for these dates Next weekend [Mar 20 - Mar 22](https://www.expedia.com/Hotel-Search?regionId=7665&startDate=2026-03-20&endDate=2026-03-22&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Mar 27 - Mar 29](https://www.expedia.com/Hotel-Search?regionId=7665&startDate=2026-03-27&endDate=2026-03-29&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Apr 10 - Apr 12](https://www.expedia.com/Hotel-Search?regionId=7665&startDate=2026-04-10&endDate=2026-04-12&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [May 8 - May 10](https://www.expedia.com/Hotel-Search?regionId=7665&startDate=2026-05-08&endDate=2026-05-10&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Wellesley guest houses ![Property entrance](https://images.trvl-media.com/lodging/2000000/1490000/1482500/1482493/ff84eaf5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hallway](https://images.trvl-media.com/lodging/2000000/1490000/1482500/1482493/99ff7575.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Studio Suite, 1 Queen Bed with Sofa bed, Kitchen | Iron/ironing board, free WiFi, bed sheets, alarm clocks](https://images.trvl-media.com/lodging/2000000/1490000/1482500/1482493/378e85d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property entrance](https://images.trvl-media.com/lodging/2000000/1490000/1482500/1482493/082b4425.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Copley House [](https://www.expedia.com/Boston-Hotels-Copley-House.h1482493.Hotel-Information) Back Bay 9.2/10 Wonderful (1,996 reviews) "Fabulous place to stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Andrea $109 nightly $126 total Mar 19 - Mar 20 Total with taxes and fees [](https://www.expedia.com/Boston-Hotels-Copley-House.h1482493.Hotel-Information) ![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 | Hypo-allergenic bedding, pillowtop beds, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/2000000/1150000/1145300/1145259/fdbe5d3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/2000000/1150000/1145300/1145259/5fb2766c.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) ### Oasis Guest House [](https://www.expedia.com/Boston-Hotels-Oasis-Guest-House.h1145259.Hotel-Information) Fenway–Kenmore 9.4/10 Exceptional (1,414 reviews) "Very friendly staff, great rooms " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Samuel $109 nightly $126 total Mar 22 - Mar 23 Total with taxes and fees [](https://www.expedia.com/Boston-Hotels-Oasis-Guest-House.h1145259.Hotel-Information) ![Outdoor spa tub](https://images.trvl-media.com/lodging/2000000/1150000/1145300/1145270/a55155e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Suite, Private Bathroom | Premium bedding, down comforters, minibar, individually decorated](https://images.trvl-media.com/lodging/2000000/1150000/1145300/1145270/44118475.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, down comforters, minibar, individually decorated](https://images.trvl-media.com/lodging/2000000/1150000/1145300/1145270/17519ab4.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) ### Clarendon Square [](https://www.expedia.com/Boston-Hotels-Clarendon-Square-Bed-Breakfast.h1145270.Hotel-Information) South End 9.2/10 Wonderful (252 reviews) "Beautiful brownstone in a great area. Stephen was very accommodating and offered advice on nearby dining. Truly one our favorite stays. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Blake $267 nightly $307 total Mar 18 - Mar 19 Total with taxes and fees [](https://www.expedia.com/Boston-Hotels-Clarendon-Square-Bed-Breakfast.h1145270.Hotel-Information) ![Property entrance](https://images.trvl-media.com/lodging/6000000/5230000/5227600/5227514/16d44f60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/6000000/5230000/5227600/5227514/aa795184.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/6000000/5230000/5227600/5227514/48469faa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/6000000/5230000/5227600/5227514/c5614d58.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Coolidge Corner Guest House [](https://www.expedia.com/Boston-Hotels-Coolidge-Corner-Guest-House.h5227514.Hotel-Information) Coolidge Corner 8.2/10 Very Good (630 reviews) "Very pleasant, comfortable stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Valerie $131 nightly $146 total Mar 15 - Mar 16 Total with taxes and fees [](https://www.expedia.com/Boston-Hotels-Coolidge-Corner-Guest-House.h5227514.Hotel-Information) ![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 | Shower, hair dryer, towels](https://images.trvl-media.com/lodging/1000000/890000/889800/889743/880d6c4e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![King Room @ 1087 Beacon St. | Desk, iron/ironing board, free WiFi, alarm clocks](https://images.trvl-media.com/lodging/1000000/890000/889800/889743/ac883cf0.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 [](https://www.expedia.com/Boston-Hotels-Beacon-Inn-1087.h889743.Hotel-Information) Longwood 8.0/10 Very Good (798 reviews) "Good services" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) DILAN $119 nightly $133 total Mar 23 - Mar 24 Total with taxes and fees [](https://www.expedia.com/Boston-Hotels-Beacon-Inn-1087.h889743.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/900000/893000/892946/c04ca267.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Double Room with One Double Bed @ 1750 Beacon St | Desk, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/1000000/900000/893000/892946/4b98a457.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![King Room @1750 Beacon St | Desk, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/1000000/900000/893000/892946/011a3ac8.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) ### Beacon Inn 1750 [](https://www.expedia.com/Boston-Hotels-Beacon-Inn-1750.h892946.Hotel-Information) Brookline 7.4/10 Good (760 reviews) "The room was clean and the staffs were nice." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Xiaoyong $109 nightly $122 total Mar 15 - Mar 16 Total with taxes and fees [](https://www.expedia.com/Boston-Hotels-Beacon-Inn-1750.h892946.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/2000000/1180000/1170200/1170159/66e5a396.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/2000000/1180000/1170200/1170159/28039a8d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/2000000/1180000/1170200/1170159/00b94875.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/2000000/1180000/1170200/1170159/d574c037.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Inn on the Horse Farm [](https://www.expedia.com/Boston-Hotels-The-Inn-On-The-Horse-Farm.h1170159.Hotel-Information) Sudbury 8.0/10 Very Good (270 reviews) "This was a beautiful place! Great for relaxation, convenient to amenities. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Melanie $88 nightly $99 total Mar 22 - Mar 23 Total with taxes and fees [](https://www.expedia.com/Boston-Hotels-The-Inn-On-The-Horse-Farm.h1170159.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) ![Family Single Room | Free WiFi](https://images.trvl-media.com/lodging/115000000/114180000/114173800/114173750/d2e2944d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Combined shower/tub, soap, toilet paper](https://images.trvl-media.com/lodging/115000000/114180000/114173800/114173750/4980475e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Family Single Room | Free WiFi](https://images.trvl-media.com/lodging/115000000/114180000/114173800/114173750/7afaca5e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 184 Heath St [](https://www.expedia.com/Boston-Hotels-184-Heath-St.h114173750.Hotel-Information) Jamaica Plain 3.4/10 (45 reviews) "It was nice. The room has wi-fi and a kitchen near the living room. There's a pool table. The owner is very nice and respectable. The other guests are quiet and it felt pretty safe. The price was really good. Thank you." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Shakari $128 nightly $147 total Mar 15 - Mar 16 Total with taxes and fees [](https://www.expedia.com/Boston-Hotels-184-Heath-St.h114173750.Hotel-Information) ![Classic Room | Free WiFi](https://images.trvl-media.com/lodging/109000000/108440000/108435200/108435179/acd5adfa.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 | Free WiFi](https://images.trvl-media.com/lodging/109000000/108440000/108435200/108435179/b86cf453.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### ESJACPE GUEST HOUSE [](https://www.expedia.com/Boston-Hotels-ESJACPE-GUEST-HOUSE.h108435179.Hotel-Information) Jamaica Plain 2.8/10 (28 reviews) "Thanks I liked my stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kristina $144 nightly $166 total Mar 15 - Mar 16 Total with taxes and fees [](https://www.expedia.com/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.com/Hotel-Search?startDate=2026-03-28&endDate=2026-03-29®ionId=7665&adults=2&lodging=GUEST_HOUSE&sort=RECOMMENDED&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.com/deals?rfrr=AA_SPRING_PROMO_7665) ![](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.com/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FWellesley-Guest-Houses.d7665-aaGuestHouses.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.com/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWellesley-Guest-Houses.d7665-aaGuestHouses.Travel-Guide-Accommodation) ## Top Wellesley Hotel Reviews ![citizenM Boston North Station](https://images.trvl-media.com/lodging/34000000/33880000/33870600/33870542/f2f31351_y.jpg) ### citizenM Boston North Station 8/10 Good "Staff was amazing. Very eclectic hotel. Room was very small but the bed was cozy(feel bad for housekeeping making those beds). Toilet creeked loudly when you sat on it (wall mounted). Breakfast was good. We would stay again if we came to a game. " [](https://expedia.com/Boston-Hotels-CitizenM-Boston-North-Station.h33870542.Hotel-Information) ![The Dagny Boston](https://images.trvl-media.com/lodging/1000000/160000/151300/151201/4c15d693_y.jpg) ### The Dagny Boston 10/10 Excellent "Great location for walking to sites and shops, in the heart of downtown. Our room was super comfortable and wonderful natural light with windows to views of downtown buildings. Restaurant and coffee shop both great! Staff was very friendly and helpful. We would recommend this hotel and would stay here again." [](https://expedia.com/Boston-Hotels-Hilton-Boston-DowntownFaneuil-Hall.h151201.Hotel-Information) ![Hilton Boston Logan Airport](https://images.trvl-media.com/lodging/1000000/290000/281600/281536/7fd62fb9_y.jpg) ### Hilton Boston Logan Airport 10/10 Excellent "Such a convenience when you have an early morning flight. Food in their restaurant is excellent too" [](https://expedia.com/Boston-Hotels-Hilton-Boston-Logan-Airport.h281536.Hotel-Information) ![Harborside Inn Of Boston](https://images.trvl-media.com/lodging/1000000/210000/202900/202814/f403d96c_y.jpg) ### Harborside Inn Of Boston 10/10 Excellent "Cute and comfortable great location " [](https://expedia.com/Boston-Hotels-Harborside-Inn-Of-Boston.h202814.Hotel-Information) ![Seaport Hotel Boston](https://images.trvl-media.com/lodging/1000000/80000/79900/79888/fa9777a9_y.jpg) ### Seaport Hotel Boston 10/10 Excellent "We had to stay an extra night because a blizzard canceled our flight. The hotel went above and beyond to accommodate us. Great place to get snowed in!" [](https://expedia.com/Boston-Hotels-Seaport-Hotel-Boston.h79888.Hotel-Information) ![The Midtown Hotel MOD Collection by Sonesta](https://images.trvl-media.com/lodging/1000000/10000/2900/2898/e1e25d35_y.jpg) ### The Midtown Hotel MOD Collection by Sonesta 10/10 Excellent " Nice cozy hotel " [](https://expedia.com/Boston-Hotels-Midtown-Hotel.h2898.Hotel-Information) ![Omni Parker House ](https://images.trvl-media.com/lodging/1000000/30000/23500/23415/de788f3d_y.jpg) ### Omni Parker House 10/10 Excellent "Beautiful historic hotel. Great resturants and bars right in the hotel lobby. Fitness center is huge. Within walking distance of many historic sites within Boston as well as food and shopping. Great central location to everything including public transportation." [](https://expedia.com/Boston-Hotels-Boston-Omni-Parker-House-Hotel.h23415.Hotel-Information) ![Encore Boston Harbor](https://images.trvl-media.com/lodging/38000000/37060000/37057200/37057112/a1d3b824_y.jpg) ### Encore Boston Harbor 10/10 Excellent "Another amazing stay. Staffs are amazing. Rooms are amazing ! I love it here " [](https://expedia.com/Boston-Hotels-Encore-Boston-Harbor.h37057112.Hotel-Information) ![The Revolution Hotel](https://images.trvl-media.com/lodging/31000000/30090000/30080300/30080227/fd67eab2_y.jpg) ### The Revolution Hotel 2/10 Terrible "This is a glorified hostel. Communal bathrooms in hall. Absurd that this would not be highlighted in property description. " [](https://expedia.com/Boston-Hotels-The-Revolution-Hotel.h30080227.Hotel-Information) ## Find out more about Wellesley ## Wellesley Guest Houses information | Number of reviews | 4,527 | | ----------------- | --------------- | | Accommodation | 16 Guest Houses | | Lowest Price | $99 | | Highest Price | $307 | ## Frequently asked questions ### What is the nightly rate for a guest house in Wellesley? ### What's the difference between a Wellesley guest house and a B&B? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - Other - [Boston Hotels ](https://www.expedia.com/Boston-Hotels.d178239.Travel-Guide-Hotels) - [Hotels near Wellesley Square Station ](https://www.expedia.com/Wellesley-Square-Station-Hotels.d6210868.Travel-Guide-Hotels) - [Hotels near Wellesley College ](https://www.expedia.com/Wellesley-College-Hotels.0-l6091825-0.Travel-Guide-Filter-Hotels) - [Hotels near Babson Park ](https://www.expedia.com/Babson-Park-Boston-Hotels.0-n183318-0.Travel-Guide-Filter-Hotels) - 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