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Oakham Vacation Rentals

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Check prices for these dates

In two weeks
Jul 17 - Jul 19
In two months
Aug 28 - Aug 30
In three months
Sep 25 - Sep 27
In four months
Oct 23 - Oct 25

Our top choices for Oakham vacation rentals

Exterior

Dove Cabin up in the Trees

Dove Cabin up in the Trees
Holland
9.8 out of 10, Exceptional, (31 reviews)
"So calm, clean and relaxing, and beautiful! Wonderful stay! "
United States
Sarah G.
The price is ￥28,419
￥41,678 total
includes taxes & fees
Jul 6 - Jul 7
Dove Cabin up in the Trees
Interior

Trainmaster's Inn - Caboose

Trainmaster's Inn - Caboose
Palmer
9.4 out of 10, Exceptional, (10 reviews)
"A great stay in a vintage RR caboose. Thanks to everyone at Trainmasters Inn!"
United States
Edward L.
The price is ￥24,290
￥56,977 total
includes taxes & fees
Jul 8 - Jul 9
Trainmaster's Inn - Caboose
Property grounds

Little House Inn - Private Home - Secluded - Ware - 2 bedroom, sleeps 6

Little House Inn - Private Home - Secluded - Ware - 2 bedroom, sleeps 6
Ware
9.8 out of 10, Exceptional, (18 reviews)
"Nice place to stay a lot of family activities on the premises short distance to shopping and attractions"
United States
Andrew
The price is ￥31,463
￥37,554 total
includes taxes & fees
Jul 2 - Jul 3
Little House Inn - Private Home - Secluded - Ware - 2 bedroom, sleeps 6
Property grounds

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
Brimfield
9.2 out of 10, Wonderful, (5 reviews)
"This is a nice place for solo travelers or a small family with kids. The kid’s bedroom has tons of games and is themed nicely. The backyard is huge but unfenced and the property is off of a busy road. Th house itself was clean and the host offered a variety of things such as slippers for the whole family, house shoes, and bath things for everyone. The house does not have a tv but the wifi works well. "
United States
Chantay-Rose
The price is ￥27,666
￥34,882 total
includes taxes & fees
Jul 2 - Jul 3
Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8
Outdoor dining

Serene 1-bedroom suite on 75 acre horse property

Serene 1-bedroom suite on 75 acre horse property
Belchertown
10.0 out of 10, Exceptional, (29 reviews)
"We had a lovely weekend, it was quiet, private and watching the horses in the pasture was wonderful. We would definitely stay again. "
United States
Kim G.
The price is ￥26,718
￥45,186 total
includes taxes & fees
Jul 27 - Jul 28
Serene 1-bedroom suite on 75 acre horse property
Smart TV, books, stereo

Newly Built Barn Loft in Pioneer Valley

Newly Built Barn Loft in Pioneer Valley
Belchertown
9.6 out of 10, Exceptional, (31 reviews)
"The place was really nice! Very clean and well decorated. We had a great short stay and would definitely book it again in the future."
United States
Emily O.
The price is ￥25,504
￥33,805 total
includes taxes & fees
Jul 8 - Jul 9
Newly Built Barn Loft in Pioneer Valley
Interior

Charming 1-bedroom apartment with AC & Breakfast in Sturbridge

Charming 1-bedroom apartment with AC & Breakfast in Sturbridge
Sturbridge
The price is ￥12,469
￥26,408 total
includes taxes & fees
Jul 4 - Jul 5
Charming 1-bedroom apartment with AC & Breakfast in Sturbridge
Living area

Clean & Cozy Private room - 3 floor_R 1

Clean & Cozy Private room - 3 floor_R 1
Union HIll
The price is ￥12,971
￥18,553 total
includes taxes & fees
Jul 12 - Jul 13
Clean & Cozy Private room - 3 floor_R 1
Smart TV

Newly Renovated 4BR Worcester Home • Pet-Friendly • Near I-290 & Park 16-2

Newly Renovated 4BR Worcester Home • Pet-Friendly • Near I-290 & Park 16-2
Worcester
10.0 out of 10, Exceptional, (4 reviews)
"Clean, perfect, had everything we needed for a quick stay "
United States
Sierra M.
The price is ￥23,949
￥62,807 total
includes taxes & fees
Jul 2 - Jul 3
Newly Renovated 4BR Worcester Home • Pet-Friendly • Near I-290 & Park 16-2
Exterior

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

Lakefront; view of ski mountain, firepit, dock, kayaks, paddle board
Westminster
9.6 out of 10, Exceptional, (37 reviews)
"Cutest home! My family loved it! "
United States
Shanna D.
The price is ￥40,650
￥90,614 total
includes taxes & fees
Jul 7 - Jul 8
Lakefront; view of ski mountain, firepit, dock, kayaks, paddle board
TV

Large 3BD 1st Floor Apartment Minutes from 290

Large 3BD 1st Floor Apartment Minutes from 290
Franklin Plantation
10.0 out of 10, Exceptional, (3 reviews)
"It was a great place for my family and i"
United States
Taisha M.
Large 3BD 1st Floor Apartment Minutes from 290
Exterior

Cottage by the Castle – Downtown Spencer

Cottage by the Castle – Downtown Spencer
Spencer
10.0 out of 10, Exceptional, (1 review)
"Wonderful stay in the cottage. Great location, and prompt and friendly communication from the owner. Beautifully kept vintage home - such a gem!"
United States
K C.
The price is ￥29,646
￥34,096 total
includes taxes & fees
Jul 8 - Jul 9
Cottage by the Castle – Downtown Spencer
3 bedrooms, iron/ironing board, free WiFi, bed sheets

Apartment in town center #1

Apartment in town center #1
West Brookfield
8.6 out of 10, Excellent, (27 reviews)
"Stayed here to visit Treehouse brewing with some friends and it was perfect. "
United States
Chris G.
The price is ￥18,217
￥55,258 total
includes taxes & fees
Jul 8 - Jul 9
Apartment in town center #1
Interior

Spacious Massachusetts Apartment #2

Spacious Massachusetts Apartment #2
West Brookfield
9.0 out of 10, Wonderful, (30 reviews)
"Really a cute place to stay, very clean and comfortable "
United States
Michelle J.
Spacious Massachusetts Apartment #2
Interior

Cozy 3BR Worcester Apt • Pet-Friendly near Clark University & I-290 4/1

Cozy 3BR Worcester Apt • Pet-Friendly near Clark University & I-290 4/1
Main South
10.0 out of 10, Exceptional, (1 review)
The price is ￥22,298
￥56,470 total
includes taxes & fees
Jul 2 - Jul 3
Cozy 3BR Worcester Apt • Pet-Friendly near Clark University & I-290 4/1
Interior

Angel Sky Challenge

Angel Sky Challenge
Worcester
2.0 out of 10, (1 review)
"The add states an entire home, this is a home with small bedrooms and a bathroom. I was under the impression by the description the entire home was ours without others on the property. I’d put that in the description I felt under comfortable with the men on the property. False advertising "
United States
Cameron R.
The price is ￥25,909
￥42,256 total
includes taxes & fees
Jul 2 - Jul 3
Angel Sky Challenge
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
Westminster
10.0 out of 10, Exceptional, (32 reviews)
"Very pleasant stay. Would definitely stay here again. "
United States
Shreya
The price is ￥55,056
￥106,227 total
includes taxes & fees
Jul 15 - Jul 16
Our pondside cabin - a charming retreat with modern amenities near Wachusett Mtn
Interior

Cozy Chic Countryside Haven - Sleeps 4 , Firepit

Cozy Chic Countryside Haven - Sleeps 4 , Firepit
Sturbridge
10.0 out of 10, Exceptional, (2 reviews)
"The place was immaculate, very large room, great kitchen, great bath, plenty of room for a family, quiet and secluded area few minutes away from town, outstanding communication with the property owner..true home away from home...Try it for yourself.."
United States
Giora Y.
The price is ￥27,042
￥54,986 total
includes taxes & fees
Jul 5 - Jul 6
Cozy Chic Countryside Haven - Sleeps 4 , Firepit
House (2 Bedrooms) | Front of property

Lakefront Cottage 2 Mi to Palladium in Worcester!

Lakefront Cottage 2 Mi to Palladium in Worcester!
3.0 star property
Worcester
The price is ￥36,272
￥73,254 total
includes taxes & fees
Jul 19 - Jul 20
Lakefront Cottage 2 Mi to Palladium in Worcester!
Property grounds

Lakefront Cottage 2 Mi to Palladium in Worcester!

Lakefront Cottage 2 Mi to Palladium in Worcester!
Worcester
9.6 out of 10, Exceptional, (15 reviews)
"Great host! Easy to contact via text. Home was clean and perfect for my family!"
United States
Michael B.
The price is ￥28,500
￥74,104 total
includes taxes & fees
Jul 19 - Jul 20
Lakefront Cottage 2 Mi to Palladium in Worcester!
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

Wellsworth Hotel

Wellsworth Hotel

10/10 Excellent
"The room was very clean. All property was very clean."
RAMON 3-night trip
Posted 5 hours ago
Wellsworth Hotel

Find out more about Oakham

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Look no further and take a look at our great range of rental properties in Oakham!

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?

Little House Inn - Private Home - Secluded - Ware - 2 bedroom, sleeps 6: This vacation home rental near Oakham is located in a rural location and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. Kick off your shoes and enjoy yourself with a garden and a selection of games.

What’s there to see and do in Oakham?

Explore the area and family-friendly sights such as EcoTarium, or get out into nature at a spot like Barre Common District. In the larger area, you’ll find Rock House Reservation and Wachusett Mountain Ski Area.

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.