Oakham Vacation Rentals

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

Vacation Rentals in Oakham

Private kitchen
Fitchburg quiet side modern 2BD.
Fitchburg quiet side modern 2BD.
10.0 out of 10, Exceptional, (1)
"The apartment was very well and thoughtfully appointed. There were four adults in our party, and there was plenty of room. There is a full kitchen and a washer and dryer furnished. Two TVs. The lounging area, fire pit, and grill area were very nice places to sit and relax, with a privacy fence all around. The owners (or managers?) were very responsive and helpful. It is an upstairs apartment, but two of our party were in our 70s and 80s, and had no problems with it. Would highly recommend!!"
United States
Roberta
Fitchburg quiet side modern 2BD.
Exterior
Dove Cabin up in the Trees
Dove Cabin up in the Trees
9.8 out of 10, Exceptional, (27)
"A sweet, cozy, nostalgic little cabin in the woods. It was the perfect stop over on our road trip to Acadia. Very peaceful, and the screened in porch was wonderful to relax on before bed and during breakfast. "
United States
Maggie G.
The price is ￥26,706
￥39,166 total
includes taxes & fees
Oct 31 - Nov 1
Dove Cabin up in the Trees
Private kitchen
Trainmaster's Inn - Caboose
Trainmaster's Inn - Caboose
9.6 out of 10, Exceptional, (8)
"A great stay in a vintage RR caboose. Thanks to everyone at Trainmasters Inn!"
United States
Edward L.
The price is ￥22,826
￥49,864 total
includes taxes & fees
Nov 2 - Nov 3
Trainmaster's Inn - Caboose
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
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
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
Fridge, microwave, oven, stovetop
New and Modern 3 B- 5 min FSU - 15 min Wachusett's
New and Modern 3 B- 5 min FSU - 15 min Wachusett's
10.0 out of 10, Exceptional, (10)
"Wonderful place to stay. Everything was very clean, comfortable, and spacious, with a warm, welcoming feel. I highly recommend the place to stay. "
United States
Catherine
The price is ￥21,830
￥50,886 total
includes taxes & fees
Nov 8 - Nov 9
New and Modern 3 B- 5 min FSU - 15 min Wachusett's
Outdoor dining
Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8
Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8
2.0 star property
The price is ￥21,304
￥27,196 total
includes taxes & fees
Nov 3 - Nov 4
Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8
Terrace/patio
Little House Inn - Private Home - Secluded - Ware - 2 bedroom, sleeps 6
Little House Inn - Private Home - Secluded - Ware - 2 bedroom, sleeps 6
2.0 star property
The price is ￥20,086
￥24,447 total
includes taxes & fees
Nov 2 - Nov 3
Little House Inn - Private Home - Secluded - Ware - 2 bedroom, sleeps 6
Outdoor spa tub
Lake House in Sturbridge w/All the Views!
Lake House in Sturbridge w/All the Views!
9.8 out of 10, Exceptional, (19)
"Thank you for a wonderful stay! Our family enjoyed the gorgeous views and the well-equipped home. There were toys, books, and games for the kids, and the beds were very comfortable. We’d definitely stay again!"
United States
Caitlin D.
The price is ￥60,868
￥140,716 total
includes taxes & fees
Nov 2 - Nov 3
Lake House in Sturbridge w/All the Views!
Terrace/patio
Apartment in town center #1
Apartment in town center #1
8.6 out of 10, Excellent, (24)
"Clean place and was well suited for what we needed"
United States
Chris
The price is ￥10,956
￥44,193 total
includes taxes & fees
Nov 4 - Nov 5
Apartment in town center #1
Exterior
Lakefront; view of ski mountain, firepit, dock, kayaks, paddle board
Lakefront; view of ski mountain, firepit, dock, kayaks, paddle board
9.6 out of 10, Exceptional, (27)
"Nice location and a very cool place to stay "
United States
Samson M.
The price is ￥22,826
￥65,939 total
includes taxes & fees
Nov 18 - Nov 19
Lakefront; view of ski mountain, firepit, dock, kayaks, paddle board
Fridge, microwave, oven, stovetop
Beautiful two-story home close to downtown worcester 5beds-4bedroom
Beautiful two-story home close to downtown worcester 5beds-4bedroom
9.0 out of 10, Wonderful, (17)
"We booked this property to stay with our adult children while visiting family nearby. The house was clean, tastefully decorated, and well maintained. It was an excellent choice for six adults to stay together!"
United States
Susi K.
The price is ￥30,130
￥63,047 total
includes taxes & fees
Nov 3 - Nov 4
Beautiful two-story home close to downtown worcester 5beds-4bedroom
Fridge, microwave, oven, stovetop
Serene 1-bedroom suite on 65 acre horse property
Serene 1-bedroom suite on 65 acre horse property
10.0 out of 10, Exceptional, (22)
"A great jumping off point for the Pioneer Valley and 5 colleges. Brent and Claire were wonderful hosts! Nice and quiet on the property, and it’s a neat experience to have the beautiful horses right outside your window. "
United States
Claire W.
The price is ￥25,189
￥43,730 total
includes taxes & fees
Nov 24 - Nov 25
Serene 1-bedroom suite on 65 acre horse property
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
Oct 31 - Nov 1
Cozy Chic Countryside Haven - Sleeps 4 , Firepit
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 ￥12,174
￥46,064 total
includes taxes & fees
Nov 2 - Nov 3
Spacious Massachusetts Apartment #2
Fridge, microwave, oven, stovetop
Like Home - BBQ, Yard, Fire Pit
Like Home - BBQ, Yard, Fire Pit
The price is ￥12,671
￥40,686 total
includes taxes & fees
Nov 4 - Nov 5
Like Home - BBQ, Yard, Fire Pit
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 3 - Nov 4
Spacious 4-bedroom with four and half bathrooms
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!
Private kitchen
4-bedroom house in nice Holden with WiFi, AC
4-bedroom house in nice Holden with WiFi, AC
The price is ￥52,042
￥108,891 total
includes taxes & fees
Oct 31 - Nov 1
4-bedroom house in nice Holden with WiFi, AC
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 2 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.