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Compare 96 Vacation Homes in Oakham with updated reviews, rates, and availability.

Beautiful & Cozy 2 BR/ 2Beds/ Netflix/Alexa/Roku.

9.8 out of 10, Exceptional, (21)
"The apartment was very clean and cozy but if you are tall watch out for the low ceilings. Being in an old home it has some wonderful character! The bed was very comfortable as well and has a nice living room with TV. I would highly recommend this place to stay. The host is also very receptive and on top of everything, thank you Ebenezer."
Beautiful & Cozy 2 BR/ 2Beds/ Netflix/Alexa/Roku.

Worcester Home on Indian Lake w/ Shared Boat Dock!

9.8 out of 10, Exceptional, (14)
"Nice place. Comfortable beds. Very clean. A little musty smell but I think we may have been the first rental this spring "
Worcester Home on Indian Lake w/ Shared Boat Dock!

Dog-Friendly Fitchburg Vacation Rental, Hike & Ski

9.4 out of 10, Exceptional, (12)
"This was our second time and definitely not the last. Great location for the ski week. Has everything you need. Pet friendly which is a big plus for us. Welcoming basket very much appreciated. "
Dog-Friendly Fitchburg Vacation Rental, Hike & Ski

Beautiful two-story home close to downtown worcester 5beds-4bedroom

8.4 out of 10, Very Good, (7)
"Big house with a good living room kitchen space. Quite neighborhood. "
The price is SAR 1,013
SAR 1,881 total
includes taxes & fees
30 Mar - 31 Mar
Beautiful two-story home close to downtown worcester 5beds-4bedroom

SunnyBrook House - 5 bedroom house in wonderful West Brookfield with WiFi, AC

SunnyBrook House - 5 bedroom house in wonderful West Brookfield with WiFi, AC

Beautiful Lakefront Home with Private Beach

9.2 out of 10, Wonderful, (166)
"Comfortable, large living areas and bedrooms. Pool table provided hours of family fun!"
Beautiful Lakefront Home with Private Beach

Spacious 4-bedroom house in charming Worcester with AC, WiFi

2.0 star property
10.0 out of 10, Exceptional, (8)
"I just wanna say that everything about the listing is on point. My cousins and I had a great snowboarding weekend at Mount Wachusett and this property was the perfect location for us. Both Spacious and Clean the property is near everything and just a 25 min drive to the slopes..Will definitely stay there again.. "
Spacious 4-bedroom house in charming Worcester with AC, WiFi

Spacious Oxford Home w/ Pool - 4 Mi to Lake!

10.0 out of 10, Exceptional, (3)
"As advertised, spacious house has everything! Very prompt property owner. We all enjoyed our stay ! "
Spacious Oxford Home w/ Pool - 4 Mi to Lake!

Brand new house close to downtown & attractions. Fenced in- Pet/family friendly

10.0 out of 10, Exceptional, (8)
"Lovely home, beautifully decorated, safe fenced yard for our furry family. Val responded immediately for something small we needed assistance wuth. Would cone back again."
Brand new house close to downtown & attractions. Fenced in- Pet/family friendly

Beautiful 2 Bedrooms with 2 Beds in Shrewsbury

9.8 out of 10, Exceptional, (33)
"Easy parking and entry even at night. Comfortable and clean."
Beautiful 2 Bedrooms with 2 Beds in Shrewsbury

Lake House in Sturbridge w/All the Views!

9.6 out of 10, Exceptional, (11)
"The property is beautiful and exactly as pictured. So much to do and such a lovely location on the lake. I wish we had been here in summer, it’s got to be spectacular. Hot tub was well cared for. Snow removal was good. Beds were comfy. Lots of dishes pots and pans. Does not include cooking supplies like oil or seasonings or cooking spray, just fyi. Awesome that we didn’t have to strip beds! Here are some notes that impacted our stay:Not thoroughly cleaned - dirty glass in one of the bedrooms,...
The price is SAR 1,444
SAR 2,752 total
includes taxes & fees
31 Mar - 1 Apr
Lake House in Sturbridge w/All the Views!

Waterfront New England House on Wickaboag Lake!

9.8 out of 10, Exceptional, (79)
"We took our Mom away for the weekend and enjoyed an evening at the Salem Cross Inn. Accommodations were nice despite the cold weather. We found the parking to be a little tricky in winter conditions due to the hill. The bedrooms were comfort and we enjoyed the ping pong table. Plenty of room around the diningroom table for games and snacking in addition to meals. Kitchen tools need updating as well as pillows, blankets and ping pong paddles. Plenty of hot water for multiple showers. Porches...
Waterfront New England House on Wickaboag Lake!

Spacious family friendly 3BR 1st FL apt. Kelly SQ, collages & universities

9.2 out of 10, Wonderful, (28)
"This was a perfect location and worked out great for our visit with out son!"
Spacious family friendly 3BR 1st FL apt. Kelly SQ, collages & universities

Sun-Dappled Retreat - Walk to Wickaboag Lake!

10.0 out of 10, Exceptional, (17)
"Excellent property in a convenient location for our family reunion "
Sun-Dappled Retreat - Walk to Wickaboag Lake!

Cozy bedrooms in Shrewsbury warm town and convenient

Cozy bedrooms in Shrewsbury warm town and convenient

Indian Lake House

8.0 out of 10, Very Good, (1)
"My stay was cozy! Loved the character."
Indian Lake House

Spacious and luxurious 3-bedroom home w/jetted bathtub

10.0 out of 10, Exceptional, (3)
"Only caveats are the air conditioning is primitive"
Spacious and luxurious 3-bedroom home w/jetted bathtub

Cozy 2-Floor Apartment with Garage Access

9.6 out of 10, Exceptional, (19)
"The unit is immaculately clean and comfortable. The host is incredibly responsive. I had a sudden and urgent need for her help. She responded to me within a few minutes and all was resolved. The unit is a short distance to WPI. Thank you."
Cozy 2-Floor Apartment with Garage Access

Wachusett Mountain Getaway - Lake Adjacent Family Home!

9.8 out of 10, Exceptional, (86)
"My niece was getting married at the Colonial Hotel. This house was only a short drive away and a great place for a family to gather. "
The price is SAR 1,313
SAR 1,626 total
includes taxes & fees
5 Apr - 6 Apr
Wachusett Mountain Getaway - Lake Adjacent Family Home!

Spacious Private Retreat Near Holyoke State Park!

10.0 out of 10, Exceptional, (7)
"It was a quite place to relax. No noise from traffic or people. Short drive to activites to do with family "
Spacious Private Retreat Near Holyoke State Park!
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.
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Other property types in Oakham

Dog-Friendly Fitchburg Vacation Rental, Hike & Ski

9.4 out of 10, Exceptional, (12)
"This was our second time and definitely not the last. Great location for the ski week. Has everything you need. Pet friendly which is a big plus for us. Welcoming basket very much appreciated. "
Dog-Friendly Fitchburg Vacation Rental, Hike & Ski

Beautiful & Cozy 2 BR/ 2Beds/ Netflix/Alexa/Roku.

9.8 out of 10, Exceptional, (21)
"The apartment was very clean and cozy but if you are tall watch out for the low ceilings. Being in an old home it has some wonderful character! The bed was very comfortable as well and has a nice living room with TV. I would highly recommend this place to stay. The host is also very receptive and on top of everything, thank you Ebenezer."
Beautiful & Cozy 2 BR/ 2Beds/ Netflix/Alexa/Roku.

Newly Built Barn Loft in Pioneer Valley

2.0 star property
8.8 out of 10, Excellent, (6)
"the unit feels new and cozy, well equipped with quality extras. Toiletries, drinks, condiments, variety of coffee and tea. My only complaint would be that the water temperature for the shower wasn't really hot.. it was reasonably warm. I personally need a HOT shower in cold winter days. Owners were understanding and kind with accidental damage we caused and the communication was smooth. "
The price is SAR 469
SAR 654 total
includes taxes & fees
30 Mar - 31 Mar
Newly Built Barn Loft in Pioneer Valley
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.