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Compare 90 Vacation Homes in Oakham with updated reviews, rates, and availability.

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

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

Worcester Home on Indian Lake w/ Shared Boat Dock!

9.8 out of 10, Exceptional, (13)
"We had a wonderful time. The home was perfect for our stay and we will stay again to enjoy the water."
Worcester Home on Indian Lake w/ Shared Boat Dock!

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

Lakefront; view of ski mountain, firepit, dock, kayaks, laundry, outdoor shower

10.0 out of 10, Exceptional, (14)
"The drive in to the property was lovely over a small one-lane bridge with a view of the mountains to the left. The house was well-appointed and beds were very comfortable. The kids loved the tv room on the second floor and the array of sleeping options."
Lakefront; view of ski mountain, firepit, dock, kayaks, laundry, outdoor shower

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

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 1,898 total
includes taxes & fees
25 Mar - 26 Mar
Beautiful two-story home close to downtown worcester 5beds-4bedroom

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.

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

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!

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

Cozy bedrooms in Shrewsbury warm town and convenient

Cozy bedrooms in Shrewsbury warm town and convenient

Home Away from Home!

10.0 out of 10, Exceptional, (2)
"Thank you for our little stay-cation! The property was beautiful and was exactly as expected. Plenty of rooms and bathrooms. My only wish was for more mirrors for us all to do our make up. But we made it work. "
The price is SAR 698
SAR 1,490 total
includes taxes & fees
25 Mar - 26 Mar
Home Away from Home!

Indian Lake House

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

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 1,463
SAR 2,759 total
includes taxes & fees
23 Mar - 24 Mar
Lake House in Sturbridge w/All the Views!

Waterfront Home with Stunning Views .. Dog friendly , and great fishing !!!

10.0 out of 10, Exceptional, (119)
"This was the best. I can't say anything bad about it. So much fun. "
Waterfront Home with Stunning Views .. Dog friendly , and great fishing !!!

Lovely 3-bedroom City Escape

9.8 out of 10, Exceptional, (19)
"Our family gets together for Christmas and this home is the ideal place for part of the family to stay."
Lovely 3-bedroom City Escape

Charming and Spacious 3-bedroom house with WiFi, AC in a quiet environment

9.4 out of 10, Exceptional, (3)
"This home was very spacious, the beds were comfortable and the area was very quiet. Great for a family getaway. There were a couple of issues with the home but our host was very responsive and accommodating. He had contacted me prior to our visit regarding these issues. There was tile dust all over the place, a cleaner was there but didn’t do a great job. Despite that we had a great time."
Charming and Spacious 3-bedroom house with WiFi, AC in a quiet environment

Beautiful Renovated Townhome w/parking

9.4 out of 10, Exceptional, (12)
"Great communication, assistance with maintenance, and receptive to feedback. Would stay again . "
Beautiful Renovated Townhome w/parking

3 Bed / 1.5 Bath Townhome

9.2 out of 10, Wonderful, (14)
"Nice house! Salted and shoveled the snow and ice!"
3 Bed / 1.5 Bath Townhome
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

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.

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

Lakefront; view of ski mountain, firepit, dock, kayaks, paddle board

9.6 out of 10, Exceptional, (19)
"for skiing wachusetts five minutes to mt..nice views from cottage on the shore -wyman pond"
Lakefront; view of ski mountain, firepit, dock, kayaks, paddle board
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.