Title: 20 Best B&B in Oakham, MA - Bed and Breakfast from $134 | Expedia.com [Oakham Travel Guide](https://expedia.com/Oakham.dx3000441390)[Hotels in Oakham](https://expedia.com/Oakham-Hotels.d3000441390.Travel-Guide-Hotels)[Vacation Rentals in Oakham](https://expedia.com/Oakham-Vacation-Rentals.d3000441390.Travel-Guide-VacationRentals)[Flights to Oakham](https://expedia.com/Cheap-Flights-To-Oakham.d3000441390.Travel-Guide-Flights)[Car Rentals in Oakham](https://expedia.com/Car-Rentals-In-Oakham.d3000441390.Car-Rental-Guide)[Oakham Vacation Packages](https://expedia.com/Oakham.d3000441390.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_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 [Feb 27 - Mar 1](https://www.expedia.com/Hotel-Search?regionId=3000441390&startDate=2026-02-27&endDate=2026-03-01&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Mar 6 - Mar 8](https://www.expedia.com/Hotel-Search?regionId=3000441390&startDate=2026-03-06&endDate=2026-03-08&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Mar 20 - Mar 22](https://www.expedia.com/Hotel-Search?regionId=3000441390&startDate=2026-03-20&endDate=2026-03-22&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Apr 17 - Apr 19](https://www.expedia.com/Hotel-Search?regionId=3000441390&startDate=2026-04-17&endDate=2026-04-19&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Oakham bed & breakfast ![Reception](https://images.trvl-media.com/lodging/18000000/17250000/17249200/17249126/eefc0b1b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, Private Bathroom (Room 4) | Egyptian cotton sheets, premium bedding, individually decorated](https://images.trvl-media.com/lodging/18000000/17250000/17249200/17249126/4779539c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/18000000/17250000/17249200/17249126/898e1cb0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, Private Bathroom (Engineers Suite) | Living area | TV](https://images.trvl-media.com/lodging/18000000/17250000/17249200/17249126/1641537b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Trainmasters Inn [](https://www.expedia.com/Palmer-Hotels-Trainmasters-Inn.h17249126.Hotel-Information) Palmer 9.6/10 Exceptional (402 reviews) "The Trainmasters Inn is a delightfully cute B&B with charm. My wife and I stayed for one night while visiting family in Springfield and loved the cozy feel and historical integrity. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nicholas $120 nightly $134 total Feb 23 - Feb 24 Total with taxes and fees [](https://www.expedia.com/Palmer-Hotels-Trainmasters-Inn.h17249126.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/110000000/109950000/109945900/109945857/24de2f4c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Separate tub and shower, towels, toilet paper](https://images.trvl-media.com/lodging/110000000/109950000/109945900/109945857/a40f345f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/110000000/109950000/109945900/109945857/d82befa0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/110000000/109950000/109945900/109945857/4ea63ac6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Inn Crowd Bed and Breakfast [](https://www.expedia.com/Holden-Hotels-The-Inn-Crowd-Bed-And-Breakfast.h109945857.Hotel-Information) Holden 10/10 Exceptional (57 reviews) "Great b&b. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) James $179 nightly $189 total Feb 23 - Feb 24 Total with taxes and fees [](https://www.expedia.com/Holden-Hotels-The-Inn-Crowd-Bed-And-Breakfast.h109945857.Hotel-Information) ![Front of property - evening/night](https://images.trvl-media.com/lodging/45000000/45000000/44999500/44999466/f1f42076.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/45000000/45000000/44999500/44999466/363b19c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/45000000/45000000/44999500/44999466/99232d9e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![BBQ/picnic area](https://images.trvl-media.com/lodging/45000000/45000000/44999500/44999466/b14e386a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Howarth House B&B [](https://www.expedia.com/Leominster-Hotels-Howarth-House-Bed-And-Breakfast.h44999466.Hotel-Information) Fitchburg 10/10 Exceptional (112 reviews) "Absolutely beautiful house. The owners are so kind and the breakfast is amazing." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) James $235 nightly $235 total Feb 23 - Feb 24 Total with taxes and fees [](https://www.expedia.com/Leominster-Hotels-Howarth-House-Bed-And-Breakfast.h44999466.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/3000000/2210000/2205700/2205666/6a4870a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds](https://images.trvl-media.com/lodging/3000000/2210000/2205700/2205666/8a97a85f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/3000000/2210000/2205700/2205666/01fdfd63.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Room, 1 Queen Bed, Private Bathroom (Wisteria Room) | Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds](https://images.trvl-media.com/lodging/3000000/2210000/2205700/2205666/4e79f11c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Maguire House Bed & Breakfast [](https://www.expedia.com/Leominster-Hotels-The-Maguire-House-Bed-Breakfast.h2205666.Hotel-Information) Ashburnham 10/10 Exceptional (36 reviews) "Wonderful bed and breakfast - and remarkable hosts! Definitely worth booking if you plan to be in the area. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ranjit $264 nightly $264 total Mar 25 - Mar 26 Total with taxes and fees [](https://www.expedia.com/Leominster-Hotels-The-Maguire-House-Bed-Breakfast.h2205666.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=2026-03-08&endDate=2026-03-09®ionId=3000441390&adults=2&lodging=BED_AND_BREAKFAST&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_3000441390) ![](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%2FOakham-Bed-And-Breakfast.d3000441390-aaBedAndBreakfast.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.com/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FOakham-Bed-And-Breakfast.d3000441390-aaBedAndBreakfast.Travel-Guide-Accommodation) ## Top Oakham Hotel Reviews ![Comfort Inn Auburn - Worcester](https://images.trvl-media.com/lodging/1000000/20000/14900/14890/223ac690_y.jpg) ### Comfort Inn Auburn - Worcester 10/10 Excellent "Very kind and helpful!" [](https://expedia.com/Worcester-Hotels-Comfort-Inn-Auburn-Worcester.h14890.Hotel-Information) ![Homewood Suites By Hilton Worcester](https://images.trvl-media.com/lodging/19000000/18160000/18157600/18157562/f7c6ce5c_y.jpg) ### Homewood Suites By Hilton Worcester 10/10 Excellent "Huge bed, spotless and clean. Outstanding breakfast, I will stay here whenever I am in Worcester. " [](https://expedia.com/Worcester-Hotels-Homewood-Suites-By-Hilton-Worcester.h18157562.Hotel-Information) ![Holiday Inn Express Hotel & Suites Auburn by IHG](https://images.trvl-media.com/lodging/2000000/1100000/1093000/1092925/ff9b3fac_y.jpg) ### Holiday Inn Express Hotel & Suites Auburn by IHG 10/10 Excellent "Great stay Staff are welcoming and do a great job Super clean room and very well appointed Especially suited for business travel " [](https://expedia.com/Worcester-Hotels-Holiday-Inn-Express-Hotel-Suites-Auburn.h1092925.Hotel-Information) ![Great Wolf Lodge Boston / Fitchburg, MA](https://images.trvl-media.com/lodging/9000000/8460000/8458800/8458771/19aa1fc1_y.jpg) ### Great Wolf Lodge Boston / Fitchburg, MA 10/10 Excellent "Clean room, staff very attentive, staff very courteous, and the food was exceptional. Everything ran perfectly for the kids. " [](https://expedia.com/Leominster-Hotels-Great-Wolf-Lodge-Boston-Fitchburg.h8458771.Hotel-Information) ![Holiday Inn Express & Suites Sturbridge by IHG](https://images.trvl-media.com/lodging/19000000/18430000/18420700/18420686/fb3b59fc_y.jpg) ### Holiday Inn Express & Suites Sturbridge by IHG 10/10 Excellent "Room was clean and spacious. Breakfast was hot and there were plenty of options." [](https://expedia.com/Sturbridge-Hotels-Holiday-Inn-Express-Suites-Sturbridge.h18420686.Hotel-Information) ![Beechwood Hotel](https://images.trvl-media.com/lodging/1000000/30000/26900/26897/e056ede9_y.jpg) ### Beechwood Hotel 10/10 Excellent "This is a gorgeous hotel!" [](https://expedia.com/Worcester-Hotels-Beechwood-Hotel.h26897.Hotel-Information) ![Doubletree by Hilton Hotel Leominster](https://images.trvl-media.com/lodging/1000000/20000/16700/16645/7570cba8_y.jpg) ### Doubletree by Hilton Hotel Leominster 10/10 Excellent "Very good " [](https://expedia.com/Leominster-Hotels-Doubletree-By-Hilton-Hotel-Leominster.h16645.Hotel-Information) ![Wellsworth Hotel](https://images.trvl-media.com/lodging/1000000/900000/894300/894252/61dc8b11_y.jpg) ### Wellsworth Hotel 10/10 Excellent "Room was clean and neat, the staff courteous and helpful. " [](https://expedia.com/Sturbridge-Hotels-Southbridge-Hotel-And-Conference-Center.h894252.Hotel-Information) ![The Colonial Hotel](https://images.trvl-media.com/lodging/1000000/50000/40500/40458/e0570769_y.jpg) ### The Colonial Hotel 10/10 Excellent "Room was clean, bed was nice" [](https://expedia.com/Leominster-Hotels-The-Colonial-Hotel.h40458.Hotel-Information) ## Find out more about Oakham ## Oakham B&B information | Number of reviews | 602 | | ----------------- | ----- | | Accommodation | 4 B&B | | Lowest Price | $134 | | Highest Price | $264 | ## Frequently asked questions ### What is the nightly rate for a Bed & Breakfast in Oakham? ### When is the best time to book a B&B in Oakham? > In particular, June is the most popular month to visit Oakham. During this time, you can expect a bustling atmosphere, with local festivals and events celebrating the season. It's a great opportunity to immerse yourself in the community while enjoying the stunning views and recreational activities the area has to offer. > > > If you're looking for a more budget-friendly option, consider visiting in late September, when the summer crowds have dispersed. This period offers a quieter experience, allowing for peaceful exploration of scenic trails and local parks, all while enjoying the crisp autumn air and the changing foliage. ### What is the difference between a Oakham Bed & Breakfast and a hotel? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - [Resorts in Rutland ](https://www.expedia.com/Rutland-Resorts.d3000441485-aaResorts.Travel-Guide-Accommodation) - [Rv Parks in Rutland ](https://www.expedia.com/Rutland-RV-Parks.d3000441485-aaRVParks.Travel-Guide-Accommodation) - [Motels in Rutland ](https://www.expedia.com/Rutland-Motels.d3000441485-aaMotels.Travel-Guide-Accommodation) - [B&B in Rutland ](https://www.expedia.com/Rutland-Bed-And-Breakfast.d3000441485-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Hotels near Saint Joseph's Abbey ](https://www.expedia.com/Saint-Josephs-Abbey-Hotels.0-l553248621532666789-0.Travel-Guide-Filter-Hotels) - [New Braintree Hotels ](https://www.expedia.com/New-Braintree-Hotels.d553248634998868294.Travel-Guide-Hotels) - 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