Oakham Vacation Rentals

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Check prices for these dates

Tonight
Oct 30 - Oct 31
Tomorrow
Oct 31 - Nov 1
This weekend
Oct 31 - Nov 2
Next weekend
Nov 7 - Nov 9

Vacation Rentals in Oakham

Fridge, microwave, oven, stovetop
Spacious 4-bedroom with four and half bathrooms
Spacious 4-bedroom with four and half bathrooms
10.0 out of 10, Exceptional, (4)
"We needed a place to stay while our hardwood floors were being refinished and this was perfect. We have a dog and 2 cats and there was plenty of space. The house was clean and as advertised."
United States
Deb H.
The price is ￥41,847
￥78,199 total
includes taxes & fees
Nov 5 - Nov 6
Spacious 4-bedroom with four and half bathrooms
Lake
Beautiful Lakefront Home with Private Beach
Beautiful Lakefront Home with Private Beach
9.4 out of 10, Exceptional, (178)
"Great location for the family. Grandson enjoyed fishing and family swimming, cookouts and fire pit. "
United States
PeterJanet S.
Beautiful Lakefront Home with Private Beach
Exterior
Dove Cabin up in the Trees
Dove Cabin up in the Trees
9.8 out of 10, Exceptional, (27)
"Great little getaway - Owners are very friendly and accommodating "
United States
Sharon S.
The price is ￥26,792
￥39,292 total
includes taxes & fees
Oct 31 - Nov 1
Dove Cabin up in the Trees
Smart TV, fireplace
Home Away from Home!
Home Away from Home!
9.4 out of 10, Exceptional, (13)
"The property was nice and accommodating for my family! "
United States
Ykeca M.
The price is ￥28,304
￥60,085 total
includes taxes & fees
Nov 2 - Nov 3
Home Away from Home!
Property grounds
Convenient, clean and cozy 3 bedroom, 2 bath overlooking idyllic lake whittemore
Convenient, clean and cozy 3 bedroom, 2 bath overlooking idyllic lake whittemore
10.0 out of 10, Exceptional, (199)
"Water front was a perfectly serene escape. House was cute and had everything we needed for a quiet getaway. Would absolutely stay here again. "
United States
Rich L.
Convenient, clean and cozy 3 bedroom, 2 bath overlooking idyllic lake whittemore
Exterior
Spacious Massachusetts Apartment #2
Spacious Massachusetts Apartment #2
9.0 out of 10, Wonderful, (28)
"We used both apartments for time with extended family. Nice to be in the same building."
United States
Tyler K.
The price is ￥12,213
￥46,212 total
includes taxes & fees
Nov 2 - Nov 3
Spacious Massachusetts Apartment #2
Smart TV, books, stereo
Newly Built Barn Loft in Pioneer Valley
Newly Built Barn Loft in Pioneer Valley
2.0 star property
9.4 out of 10, Exceptional, (20)
"cute little place! host was very responsive"
United States
zane s.
The price is ￥24,044
￥32,353 total
includes taxes & fees
Nov 2 - Nov 3
Newly Built Barn Loft in Pioneer Valley
Interior
One Bedroom Apartment with Separate Bunk Bed Area
One Bedroom Apartment with Separate Bunk Bed Area
9.6 out of 10, Exceptional, (23)
"My family had a wonderful stay! We attended a weekend event at WPI and this was a great location to rest after a long day. Our kids especially enjoyed the large TV in the living room. It was clean and communication/ instructions were clear. Thanks! "
United States
Katie M.
One Bedroom Apartment with Separate Bunk Bed Area
Exterior
Hillside Hideaway: full family home, 250 ft from the lake shore. Dog friendly!
Hillside Hideaway: full family home, 250 ft from the lake shore. Dog friendly!
10.0 out of 10, Exceptional, (14)
"The house was beautiful. Very clean, pet friendly, very good communication with owner."
United States
JUNE
Hillside Hideaway: full family home, 250 ft from the lake shore. Dog friendly!
Exterior
Relaxing, Holiday Retreat, Pool, fireplace
Relaxing, Holiday Retreat, Pool, fireplace
10.0 out of 10, Exceptional, (32)
"A truly beautiful place with the most gorgeous pool and landscaping. We will be back for sure!"
United States
Danneel A.
Relaxing, Holiday Retreat, Pool, fireplace
Children's area
Beautiful & Cozy 2 BR/ 2Beds/ Netflix/Alexa/Roku.
Beautiful & Cozy 2 BR/ 2Beds/ Netflix/Alexa/Roku.
9.6 out of 10, Exceptional, (30)
"I stayed at this property for almost a month and thoroughly enjoyed it. It had everything I needed and is conveniently located to Route 9 and I-435. The host was very responsive, which I greatly appreciated. It's nice to know such a comfortable place is available in Shrewsbury."
United States
Patty S.
Beautiful & Cozy 2 BR/ 2Beds/ Netflix/Alexa/Roku.
Interior
Cottage on Partridge Pond
Cottage on Partridge Pond
10.0 out of 10, Exceptional, (25)
"Was a little nervous with the square footage but boy they have maximized every inch of this house. Lake was glorious, rooms were comfortable and all the extras were top notch. Already booked another stay for later this year. Such a perfect place for our family."
United States
Jessica K.
Cottage on Partridge Pond
Exterior
SalsVista 2nd Floor Corner Apt
SalsVista 2nd Floor Corner Apt
10.0 out of 10, Exceptional, (4)
"We very much enjoyed our weekend stay at this place. The apartment was immaculate and very comfortable."
United States
Anonymous traveler
SalsVista 2nd Floor Corner Apt
Smart TV
Our pondside cabin - a charming retreat with modern amenities near Wachusett Mtn
Our pondside cabin - a charming retreat with modern amenities near Wachusett Mtn
10.0 out of 10, Exceptional, (22)
"Kathleen was an amazing host and the property exceeded our expectations. The kids loved the bunk room and loft and the surrounding area provided something for all interests. We will definitely be planning another stay. "
United States
Michael T.
The price is ￥34,349
￥78,376 total
includes taxes & fees
Nov 6 - Nov 7
Our pondside cabin - a charming retreat with modern amenities near Wachusett Mtn
Fridge, microwave, oven, stovetop
Spacious 4-bedroom house in charming Worcester with AC, WiFi
Spacious 4-bedroom house in charming Worcester with AC, WiFi
2.0 star property
10.0 out of 10, Exceptional, (21)
"Great space to hang out with family while in town. "
United States
Blessing T.
Spacious 4-bedroom house in charming Worcester with AC, WiFi
Fridge, microwave, oven, stovetop
Beautiful 2 Bedrooms with 2 Beds in Shrewsbury
Beautiful 2 Bedrooms with 2 Beds in Shrewsbury
9.8 out of 10, Exceptional, (39)
"Our stay was wonderful. The house was adorable and had everything we needed. The host was always on top of messaging back if we had a question and was very polite. "
United States
Traci M.
Beautiful 2 Bedrooms with 2 Beds in Shrewsbury
Dining
Large relaxing house in 25 acres of private woods with lake access.
Large relaxing house in 25 acres of private woods with lake access.
9.6 out of 10, Exceptional, (24)
"Beautiful place and we had a great family weekend"
United States
William M.
Large relaxing house in 25 acres of private woods with lake access.
Terrace/patio
Direct waterfront Lake House, stunning views Sleeps 8 on a private PENINSULA!
Direct waterfront Lake House, stunning views Sleeps 8 on a private PENINSULA!
9.8 out of 10, Exceptional, (88)
"We rented this property because our was getting married in Sturbridge and we wanted a place for the groomsmen to gather and get ready but also where we could spend the night. The location was awesome! ( can’t wait to see pictures) and the host was friendly and quick to respond. We enjoyed it so much that we are already talking about returning for a relaxing visit!!"
United States
Wendy U.
Direct waterfront Lake House, stunning views Sleeps 8 on a private PENINSULA!
Interior
New renovation cozy house in Worcester
New renovation cozy house in Worcester
2.0 star property
9.8 out of 10, Exceptional, (14)
"A very lovely stay , calm and quiet "
United States
Alex R.
New renovation cozy house in Worcester
1 bedroom, iron/ironing board, WiFi, bed sheets
Cozy Chic Countryside Haven - Sleeps 4 , Firepit
Cozy Chic Countryside Haven - Sleeps 4 , Firepit
2.0 star property
The price is ￥35,760
￥64,251 total
includes taxes & fees
Nov 12 - Nov 13
Cozy Chic Countryside Haven - Sleeps 4 , Firepit
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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Top Oakham Hotel Reviews

Publick House Historic Inn and Country Motor Lodge

Publick House Historic Inn and Country Motor Lodge

10/10 Excellent
"We had a good time "
Robert 2-night trip
Posted 3 days ago
Publick House Historic Inn and Country Motor Lodge

Find out more about Oakham

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Frequently asked questions

Are there vacation rentals in Oakham?

Yes, we give you a choice of vacation rentals near well known attractions in Oakham, or you can select a more remote option if you're looking for relaxation.

What are some of the best vacation rentals in Oakham?

Spacious 4-bedroom with four and half bathrooms: This vacation home rental near Oakham is equipped with a garden, air-conditioning, and laundry facilities to help you feel comfortable during your stay. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

What’s there to see and do in Oakham?

Explore the area and family-friendly sights such as Green Hill Park, or get out into nature at a spot like Rock House Reservation. In the larger area, you’ll find Hardwick Vineyard and Winery and Wachusett Mountain State Reservation.

What’s a vacation rental in Oakham like?

Vacation rentals are private properties where you can stay for a couple of days or more in Oakham. Vacation rentals feature amenities like laundry facilities and kitchens so your stay will be comfortable. If you're concerned about cleanliness, a vacation rental can provide a sense of safety away from public hotel elevators and busy reception areas while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a great choice for a small group gathering.