Title: 20 Best B&B in Oakham, MA - Bed and Breakfast from $121 | 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 [Mar 13 - Mar 15](https://www.expedia.com/Hotel-Search?regionId=3000441390&startDate=2026-03-13&endDate=2026-03-15&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [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 one month [Apr 3 - Apr 5](https://www.expedia.com/Hotel-Search?regionId=3000441390&startDate=2026-04-03&endDate=2026-04-05&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [May 1 - May 3](https://www.expedia.com/Hotel-Search?regionId=3000441390&startDate=2026-05-01&endDate=2026-05-03&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 (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) ![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 (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) ### Trainmasters Inn [](https://www.expedia.com/Palmer-Hotels-Trainmasters-Inn.h17249126.Hotel-Information) Palmer 9.6/10 Exceptional (403 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 $108 nightly $121 total Mar 4 - Mar 5 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) ![Reception](https://images.trvl-media.com/lodging/110000000/109950000/109945900/109945857/4ea63ac6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/110000000/109950000/109945900/109945857/227a4201.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) ### 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 $176 nightly $187 total Mar 4 - Mar 5 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) ![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) ![Interior](https://images.trvl-media.com/lodging/45000000/45000000/44999500/44999466/363b19c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![North Superior Room, 1 Queen Bed, Garden View | Premium bedding, individually furnished, laptop workspace](https://images.trvl-media.com/lodging/45000000/45000000/44999500/44999466/079f83fd.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 Mar 4 - Mar 5 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) ![Fireplace](https://images.trvl-media.com/lodging/3000000/2210000/2205700/2205666/56f95948.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) ![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 $261 nightly $261 total Mar 18 - Mar 19 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=2026-03-17&endDate=2026-03-18®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 ![Holiday Inn Express Hotel & Suites Auburn by IHG](https://images.trvl-media.com/lodging/2000000/1100000/1093000/1092925/232f580c_y.jpg) ### Holiday Inn Express Hotel & Suites Auburn by IHG 6/10 Okay "Room was fine; shower had very weak water pressure. ;/" [](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 2/10 Terrible "´" [](https://expedia.com/Leominster-Hotels-Great-Wolf-Lodge-Boston-Fitchburg.h8458771.Hotel-Information) ![Beechwood Hotel](https://images.trvl-media.com/lodging/1000000/30000/26900/26897/e056ede9_y.jpg) ### Beechwood Hotel 10/10 Excellent "Overall excellent on all fronts" [](https://expedia.com/Worcester-Hotels-Beechwood-Hotel.h26897.Hotel-Information) ![The Colonial Hotel](https://images.trvl-media.com/lodging/1000000/50000/40500/40458/e0570769_y.jpg) ### The Colonial Hotel 4/10 Poor "This property needs a serious update. The property looks tired. Attempted to use the fitness room and it was dirty and much of the equipment was unusable. The pool and jacuzzi were closed and looked disgusting. The common areas and room felt unclean " [](https://expedia.com/Leominster-Hotels-The-Colonial-Hotel.h40458.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 "All of the above. Only problem I had is not getting my essentials, money back. The hotel issued it right back to me, but it's not right I still haven't got my money. This is the best hotel I've been to. Ty to Moe and John and McKenzie @ the front desk.you can't find better people and great service they also have the best breakfast ive ever seen in my life a lot too choose from. Ty Melinda remillard " [](https://expedia.com/Sturbridge-Hotels-Holiday-Inn-Express-Suites-Sturbridge.h18420686.Hotel-Information) ![Wellsworth Hotel](https://images.trvl-media.com/lodging/1000000/900000/894300/894252/61dc8b11_y.jpg) ### Wellsworth Hotel 8/10 Good "Clean room Beautiful hotel " [](https://expedia.com/Sturbridge-Hotels-Southbridge-Hotel-And-Conference-Center.h894252.Hotel-Information) ![Courtyard by Marriott Worcester](https://images.trvl-media.com/lodging/1000000/330000/327500/327432/bc28e58e_y.jpg) ### Courtyard by Marriott Worcester 6/10 Okay "The room was very nice. Our room had been recently renovated, and everything was clean and neat when we arrived. Breakfast the following morning, however, was a total train wreck. Whereas most hotels have a self-serve variety of food available, we had to wait in line to place an order with a short order cook. There were three or four other people in front of us. After waiting for more than 30 minutes there was STILL one person in line ahead of us. The problem is that there was only one person taking orders AND cooking all of the food by herself. Poor woman. At this point, we had to leave so we'd be able to make it to our appointment on time - there was no way we'd be able to spend more time waiting just to place an order, then wait MORE time for it to be cooked, and then be able to sit and eat. When we complained at the front desk, we were told that the delay was because they were very busy. Uhm - that's kind of the definition of a hotel on a Saturday morning when breakfast is only available for two hours. Breakfast was a total FAIL. At any other hotel, we would have served ourselves and been gone inside of 10 mins." [](https://expedia.com/Worcester-Hotels-Courtyard-By-Marriott-Worcester.h327432.Hotel-Information) ![Homewood Suites By Hilton Worcester](https://images.trvl-media.com/lodging/19000000/18160000/18157600/18157562/c9f00036_y.jpg) ### Homewood Suites By Hilton Worcester 4/10 Poor "Room was fine, but customer service was atrocious (other than a gentleman named Shay)" [](https://expedia.com/Worcester-Hotels-Homewood-Suites-By-Hilton-Worcester.h18157562.Hotel-Information) ![Hampton Inn Auburn](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066413/afddbde6_y.jpg) ### Hampton Inn Auburn 10/10 Excellent "Place was very clean! " [](https://expedia.com/Worcester-Hotels-Hampton-Inn-Auburn.h1066413.Hotel-Information) ## Find out more about Oakham ## Oakham B&B information | Number of reviews | 608 | | ----------------- | ----- | | Accommodation | 4 B&B | | Lowest Price | $121 | | Highest Price | $261 | ## 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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