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Compare 95 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, (15)
"Clean, beautiful home"
Worcester Home on Indian Lake w/ Shared Boat Dock!

Dog-Friendly Fitchburg Vacation Rental, Hike & Ski

9.4 out of 10, Exceptional, (16)
"We stayed at the property for four nights and it was as a base for our daughter's college tours in Massachusetts. The property was located perfectly for us. The location is both secluded and close to all amenities like groceries, trails and other natural attractions. The property is perfectly setup with charming touches, nicely furnished. It has everything you need to have a very comfortable stay. Bedrooms are cozy with good closet space. All the rooms has TV so we could watch different sports...
Dog-Friendly Fitchburg Vacation Rental, Hike & Ski

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

10.0 out of 10, Exceptional, (1)
"We had the most amazing time at Gail’s place. It was even more special, more beautiful, cozy and welcoming than the pictures or descriptions could capture. It is a home, in the very best of ways. Especially in early Spring volatile weather, when it was perfect to be cozy inside, cook, play games, rest. The beds were all comfortable, as was the seating, the space. Kitchen stocked, bathrooms abundant, and everything exceptionally clean. I almost recommended coming when the weather is bad, to take...
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
9.8 out of 10, Exceptional, (10)
"We thoroughly enjoyed our stay. The rooms are spacious, beds are large and comfortable with lots of pillows, kitchen is well-appointed, bathrooms clean and spacious as well, with lots of towels and even make-up removal washcloths. We had 6 adults and one child in our group so that 2 full and 1 half bathroom met our needs really well.When we had a surprise snow storm (in April!), Denys responded to our call immediately and remotely unlocked the garage so we could access the snow shovel! We...
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, (4)
"A very nice, clean, spacious New England home. The owner of the property was very easy to communicate with. We live in Florida but my wife and I are originally from the area. We went to visit family but knew we needed to find accomodations for our family of 5. The house was perfect and if it is available the next time we visit we'll definitely be staying there. "
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 AED 1,433
AED 2,718 total
includes taxes & fees
27 Apr - 28 Apr
Lake House in Sturbridge w/All the Views!

Waterfront New England House on Wickaboag Lake!

9.8 out of 10, Exceptional, (80)
"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, (21)
"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 Home! Near 1761 Old Mill and Trails!

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. "
Wachusett Mountain Getaway, Lake Adjacent Home! Near 1761 Old Mill and Trails!

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!

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 !!!
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.

completely renovated 3 bedroom, 2 bath overlooking idyllic lake whittemore

10.0 out of 10, Exceptional, (182)
"We have used this property for over 4 years now. Just love it and the o"
completely renovated 3 bedroom, 2 bath overlooking idyllic lake whittemore

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 AED 683
AED 1,467 total
includes taxes & fees
28 Apr - 29 Apr
Home Away from Home!
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.