Search Vacation Homes in Oakham

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

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, (15)
"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, (13)
"We drove from Wisconsin to bring one child back to The Winchendon School and to tour Curry College for another. We planned to be back and forth a lot and found the location of this property decent. Our goal with renting a property is to prepare our own meals and to have a comfortable space. The kitchen had basic supplies/equipment. The pans could be updated due to heavily scratched coating, although they worked ok. I found some of the utensils to be dirty, especially the pizza cutter. I am...
Dog-Friendly Fitchburg Vacation Rental, Hike & Ski

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

8.4 out of 10, Very Good, (8)
"Nice place."
The price is SAR 1,013
SAR 1,915 total
includes taxes & fees
30 Apr - 1 May
Beautiful two-story home close to downtown worcester 5beds-4bedroom

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
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, (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 SAR 1,651
SAR 3,006 total
includes taxes & fees
20 Apr - 21 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, (20)
"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

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.
Don't see what you're looking for?
See all available properties in Oakham
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Oakham

Dog-Friendly Fitchburg Vacation Rental, Hike & Ski

9.4 out of 10, Exceptional, (13)
"We drove from Wisconsin to bring one child back to The Winchendon School and to tour Curry College for another. We planned to be back and forth a lot and found the location of this property decent. Our goal with renting a property is to prepare our own meals and to have a comfortable space. The kitchen had basic supplies/equipment. The pans could be updated due to heavily scratched coating, although they worked ok. I found some of the utensils to be dirty, especially the pizza cutter. I am...
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.

completely renovated 3 bedroom, 2 bath overlooking idyllic lake whittemore

10.0 out of 10, Exceptional, (183)
"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
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.