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Oakham Vacation Rentals

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Check prices for these dates

In two weeks
31 Jul - 2 Aug
In two months
11 Sep - 13 Sep
In three months
9 Oct - 11 Oct
In four months
6 Nov - 8 Nov

Our top choices for Oakham vacation rentals

Living area

Clean & Cozy Private- 3 floor_R 4

Clean & Cozy Private- 3 floor_R 4
Union HIll
The price is AED 294
AED 421 total
includes taxes & fees
18 Jul - 19 Jul
Clean & Cozy Private- 3 floor_R 4
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 AED 645
AED 945 total
includes taxes & fees
20 Jul - 21 Jul
Dove Cabin up in the Trees
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
9.6 out of 10, Exceptional, (20 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 AED 661
AED 788 total
includes taxes & fees
20 Jul - 21 Jul
Little House Inn - Private Home - Secluded - Ware - 2 bedroom, sleeps 6
Interior

Spacious Massachusetts Apartment #2

Spacious Massachusetts Apartment #2
West Brookfield
9.2 out of 10, Wonderful, (31 reviews)
"Really a cute place to stay, very clean and comfortable "
United States
Michelle J.
The price is AED 436
AED 1,283 total
includes taxes & fees
19 Jul - 20 Jul
Spacious Massachusetts Apartment #2
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, (32 reviews)
"Kitchen was clean and well stocked with water, and some small snacks. "
United States
Cheyenne K.
The price is AED 579
AED 778 total
includes taxes & fees
19 Jul - 20 Jul
Newly Built Barn Loft in Pioneer Valley
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 AED 551
AED 1,264 total
includes taxes & fees
28 Jul - 29 Jul
Trainmaster's Inn - Caboose
Property grounds

Lakefront Cottage 2 Mi to Palladium in Worcester!

Lakefront Cottage 2 Mi to Palladium in Worcester!
Worcester
9.8 out of 10, Exceptional, (17 reviews)
"The property was well kept, easy to get to, and close to where we needed to be."
United States
Dustin K.
The price is AED 646
AED 1,686 total
includes taxes & fees
19 Jul - 20 Jul
Lakefront Cottage 2 Mi to Palladium in Worcester!
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, (30 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 AED 438
AED 851 total
includes taxes & fees
19 Jul - 20 Jul
Serene 1-bedroom suite on 75 acre horse property
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, (33 reviews)
"Very pleasant stay. Would definitely stay here again. "
United States
Shreya
The price is AED 918
AED 1,999 total
includes taxes & fees
5 Aug - 6 Aug
Our pondside cabin - a charming retreat with modern amenities near Wachusett Mtn
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 AED 588
AED 958 total
includes taxes & fees
18 Jul - 19 Jul
Angel Sky Challenge
3 bedrooms, iron/ironing board, WiFi (free), bed sheets

Apartment in town center #1

Apartment in town center #1
West Brookfield
8.8 out of 10, Excellent, (28 reviews)
"Stayed here to visit Treehouse brewing with some friends and it was perfect. "
United States
Chris G.
The price is AED 397
AED 1,231 total
includes taxes & fees
22 Jul - 23 Jul
Apartment in town center #1
Interior

Charming 1-bedroom apartment with AC & Breakfast in Sturbridge

Charming 1-bedroom apartment with AC & Breakfast in Sturbridge
Sturbridge
The price is AED 220
AED 529 total
includes taxes & fees
20 Jul - 21 Jul
Charming 1-bedroom apartment with AC & Breakfast in Sturbridge
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 AED 551
AED 1,169 total
includes taxes & fees
19 Jul - 20 Jul
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 AED 823
AED 1,662 total
includes taxes & fees
19 Jul - 20 Jul
Lakefront Cottage 2 Mi to Palladium in Worcester!
Exterior

Cottage by the Castle – Downtown Spencer

Cottage by the Castle – Downtown Spencer
Spencer
10.0 out of 10, Exceptional, (2 reviews)
"Nice, clean and well maintained. Would stay here again."
United States
Sarah S.
The price is AED 841
AED 961 total
includes taxes & fees
28 Jul - 29 Jul
Cottage by the Castle – Downtown Spencer
Dining

Beautiful Worcester Downtown King Bd/Office World Cup Boston

Beautiful Worcester Downtown King Bd/Office World Cup Boston
Worcester
10.0 out of 10, Exceptional, (2 reviews)
"I had an amazing stay here and would absolutely recommend this place to anyone visiting Boston or Worcester, Massachusetts. The house was truly 100% excellent. Everything was incredibly clean, spacious, and well organized. I loved the kitchen, my room, and the bathroom, everything was spotless and very comfortable. Honestly, the entire home was sparkling clean and very welcoming.I also slept extremely well during my stay. The bed, pillows, and bedding were so comfortable, which made the...
United States
Masard T.
The price is AED 551
AED 1,261 total
includes taxes & fees
17 Aug - 18 Aug
Beautiful Worcester Downtown King Bd/Office World Cup Boston
3 bedrooms, WiFi

Newly Refreshed 3bd Spacious Unit Minutes from 290

Newly Refreshed 3bd Spacious Unit Minutes from 290
Franklin Plantation
9.4 out of 10, Exceptional, (3 reviews)
"The communication was wonderful. There were some things that needed to be addressed and they were.We would definitely rent again! The space is very spacious and clean"
United States
Anonymous traveler
The price is AED 459
AED 1,047 total
includes taxes & fees
20 Jul - 21 Jul
Newly Refreshed 3bd Spacious Unit Minutes from 290
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, (7 reviews)
"Welcoming, cute."
United States
Trinity M.
The price is AED 698
AED 866 total
includes taxes & fees
12 Aug - 13 Aug
Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8
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, (38 reviews)
"Cutest home! My family loved it! "
United States
Shanna D.
The price is AED 1,102
AED 2,273 total
includes taxes & fees
30 Jul - 31 Jul
Lakefront; view of ski mountain, firepit, dock, kayaks, paddle board
Coffee/tea maker, fridge, microwave, oven

Spacious 4-bedroom with four and half bathrooms

Spacious 4-bedroom with four and half bathrooms
Worcester
10.0 out of 10, Exceptional, (12 reviews)
"Perfect location"
United States
Harmony F.
The price is AED 1,010
AED 1,879 total
includes taxes & fees
20 Jul - 21 Jul
Spacious 4-bedroom with four and half bathrooms
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

Hilton Garden Inn Worcester

Hilton Garden Inn Worcester

8/10 Good
"Nice hotel- room was spacious and comfortable and dining options were available in and around the hotel"
Fauzia 1-night trip
Posted 1 day ago
Hilton Garden Inn Worcester

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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?

Home Away from Home!: This vacation home rental near Oakham offers a fireplace, a patio, and air-conditioning to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a hot tub.

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 Hardwick Vineyard and Winery.

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.