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Oakham Vacation Rentals

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Oakham vacation rentals

The Cottage is nestled next to the historic Sagendorph Mansion.

1. Cottage by the Castle – Downtown Spencer

Cottage by the Castle – Downtown Spencer
Spencer
10.0 out of 10, Exceptional, (8 reviews)
"The cottage is beautiful, cozy and super comfortable! We loved it! The hosts also were super, communicative and friendly. The place was clean, we had everything we needed, is in a very safe area, and very pretty! Hight recommended! Thank you for hosting us!"
United States
Fabiola
The price is ￥36,229
￥41,249 total
includes taxes & fees
Oct 14 - Oct 15
Cottage by the Castle – Downtown Spencer
A grassy outdoor area with a hammock, chairs, and a stone wall.

2. 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, (27 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 ￥28,923
￥34,587 total
includes taxes & fees
Oct 14 - Oct 15
Little House Inn - Private Home - Secluded - Ware - 2 bedroom, sleeps 6
A living room with a TV, sofa, chairs, a lamp, and a window with sheer curtains.

3. Clean & Cozy Private-3 floor_R 2

Clean & Cozy Private-3 floor_R 2
Union HIll
9.0 out of 10, Wonderful, (2 reviews)
"Nice and very clean. Host communicated fast and helpful."
United States
Ekaterina
The price is ￥12,681
￥18,138 total
includes taxes & fees
Oct 14 - Oct 15
Clean & Cozy Private-3 floor_R 2
A modern kitchen with white cabinets, a stainless steel refrigerator, and a dining area with a table and chairs.

4. Cozy Chic Countryside Haven - Sleeps 4 , Firepit

Cozy Chic Countryside Haven - Sleeps 4 , Firepit
Sturbridge
10.0 out of 10, Exceptional, (3 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 ￥23,747
￥49,867 total
includes taxes & fees
Oct 14 - Oct 15
Cozy Chic Countryside Haven - Sleeps 4 , Firepit
A compact, modern laundry room with a built-in washer and dryer, a small storage cabinet, and a tiled floor.

5. 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 ￥25,330
￥41,311 total
includes taxes & fees
Oct 14 - Oct 15
Angel Sky Challenge
A stone wall, a metal gate, and a building with a blue door and a number '74' sign.

6. A Timeless Retreat at Historic Crompton House

A Timeless Retreat at Historic Crompton House
Elm Park
10.0 out of 10, Exceptional, (1 review)
"This is a beautiful property! Great location and amazing hosts! We had everything we needed and were very comfortable. I highly recommend this place!"
United States
Jessica H.
A Timeless Retreat at Historic Crompton House
A spacious living room with a wooden ceiling, a grey sofa, a staircase, and a large window.

7. 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, (37 reviews)
"Very pleasant stay. Would definitely stay here again. "
United States
Shreya
The price is ￥35,620
￥81,277 total
includes taxes & fees
Oct 22 - Oct 23
Our pondside cabin - a charming retreat with modern amenities near Wachusett Mtn
A modern living room with a leather sofa, a coffee table, and a dining table. There are two windows providing natural light, a ceiling light fixture, and a trash can.

8. Newly Built Barn Loft in Pioneer Valley

Newly Built Barn Loft in Pioneer Valley
Belchertown
9.6 out of 10, Exceptional, (38 reviews)
"The host was so responsive and made sure everything was perfect! It was the cutest and most comfy set up! With an adorable town beach 5 min down the road! Highly recommend!"
United States
Nora M.
The price is ￥24,934
￥33,551 total
includes taxes & fees
Oct 14 - Oct 15
Newly Built Barn Loft in Pioneer Valley
A room with two black leather sofas, a glass-top coffee table, white walls, and a ceiling light.

9. Modern Stay 3BR Worcester Apt • FREE Parking near Clark University & I-290 4/1

Modern Stay 3BR Worcester Apt • FREE Parking near Clark University & I-290 4/1
Main South
8.0 out of 10, Very good, (2 reviews)
"The host was very communicative and obviously has tried to make this unit a reasonable place to have people stay. However, the layout of the place was not ideal. They turned a front sitting room into a bedroom, but it doesn't really work well. Further, that room smelled like marijuana our whole stay (1-night). It connected to the stairwell up to the units above, and my guess is that those people just smoke weed all day/night and it's impacting this unit. Further, the outside of the house is...
United States
Jeffrey B.
The price is ￥23,050
￥56,278 total
includes taxes & fees
Nov 8 - Nov 9
Modern Stay 3BR Worcester Apt • FREE Parking near Clark University & I-290 4/1
A house with a stone wall and a dock extending into a calm body of water.

10. 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, (42 reviews)
"Very clean and tidy!Tyler was great - even accommodated last minute to add our dogs to the booking!Would definitely stay again!"
United States
Christina C.
The price is ￥25,330
￥70,509 total
includes taxes & fees
Oct 15 - Oct 16
Lakefront; view of ski mountain, firepit, dock, kayaks, paddle board
A two-story residential building with a front porch, a satellite dish, and a small front yard.

11. Renovated Lakefront 5BR • Near Colleges • Sunsets • Sleeps 12

Renovated Lakefront 5BR • Near Colleges • Sunsets • Sleeps 12
Worcester
The price is ￥48,918
￥100,378 total
includes taxes & fees
Oct 26 - Oct 27
Renovated Lakefront 5BR • Near Colleges • Sunsets • Sleeps 12
A wooden gazebo with a metal roof, surrounded by a brick patio with outdoor seating.

12. 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, (38 reviews)
"Not your average stay! This place is super cool!!"
United States
Wayne B.
The price is ￥21,372
￥39,658 total
includes taxes & fees
Oct 18 - Oct 19
Serene 1-bedroom suite on 75 acre horse property
A modern kitchen with white cabinets, stainless steel appliances, and a central island with bar stools.

13. 4-bedroom house in nice Holden with WiFi, AC

4-bedroom house in nice Holden with WiFi, AC
Holden
10.0 out of 10, Exceptional, (2 reviews)
"Communication with owner was very responsive and timely. House was clean and as description. Any problems were immediately addressed by owner."
United States
larry d.
The price is ￥59,366
￥88,687 total
includes taxes & fees
Nov 9 - Nov 10
4-bedroom house in nice Holden with WiFi, AC
A room with a blue wall, a mirror, a table with chairs, potted plants, and a Christmas tree.

14. Charming 1-bedroom apartment with AC & Breakfast in Sturbridge

Charming 1-bedroom apartment with AC & Breakfast in Sturbridge
Sturbridge
The price is ￥15,039
￥29,000 total
includes taxes & fees
Oct 14 - Oct 15
Charming 1-bedroom apartment with AC & Breakfast in Sturbridge
Living area

15. 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, (6 reviews)
"Clean, perfect, had everything we needed for a quick stay "
United States
Sierra M.
The price is ￥33,688
￥74,250 total
includes taxes & fees
Nov 8 - Nov 9
Newly Renovated 4BR Worcester Home • Pet-Friendly • Near I-290 & Park 16-2
A neatly made bed with rolled towels, a bedside table with a lamp, and a large mirror on the wall.

16. 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 ￥15,198
￥39,138 total
includes taxes & fees
Nov 9 - Nov 10
Newly Refreshed 3bd Spacious Unit Minutes from 290
A living room with two sofas, a coffee table, and a bookshelf.

17. Heart of Shrewsbury St – 2BR Stay

Heart of Shrewsbury St – 2BR Stay
Shrewsbury Street
8.0 out of 10, Very good, (1 review)
"We did not receive information on how to enter the property until we arrived and called the owner. There was a lot of poison ivy growing in our parking area."
United States
Sharon
The price is ￥29,066
￥37,979 total
includes taxes & fees
Oct 20 - Oct 21
Heart of Shrewsbury St – 2BR Stay
A lakeside cabin with a dock, a boat, and a second-story deck.

18. Lakefront; view of ski mountain, firepit, dock, kayaks, laundry, outdoor shower

Lakefront; view of ski mountain, firepit, dock, kayaks, laundry, outdoor shower
Westminster
10.0 out of 10, Exceptional, (42 reviews)
"We had a great stay with our family."
United States
Sherri P.
Lakefront; view of ski mountain, firepit, dock, kayaks, laundry, outdoor shower
A living room with a round table, two armchairs, a TV mounted on the wall, and a potted plant.

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

Beautiful two-story home close to downtown worcester 5beds-4bedroom
Worcester
9.0 out of 10, Wonderful, (20 reviews)
"Great house-clean, great location."
United States
Kathleen R.
The price is ￥34,901
￥70,084 total
includes taxes & fees
Oct 31 - Nov 1
Beautiful two-story home close to downtown worcester 5beds-4bedroom
A modern kitchen with a stainless steel refrigerator, double sink, and wooden flooring.

20. Spacious 4-bedroom with four and half bathrooms

Spacious 4-bedroom with four and half bathrooms
Worcester
9.8 out of 10, Exceptional, (23 reviews)
The price is ￥43,535
￥81,354 total
includes taxes & fees
Oct 14 - Oct 15
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

Beechwood Hotel

Beechwood Hotel

10/10 Excellent
"Very nice and fancy hotel! It was lovely staying there! All hotels should look like this one. Also a reasonable price for how lovely it bwas taken cared."
Naomi 1-night trip
Posted less than an hour ago
Beechwood Hotel

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?

Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8: This vacation home rental near Oakham is located in a rural location and has a garden, a selection of games, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

What’s there to see and do in Oakham?

Explore the area and family-friendly sights such as Great Wolf Lodge Waterpark, 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.