Oakham Vacation Rentals from ￥12,802: Search Short-Term Rentals

Q: 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.

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Our top choices for Oakham vacation rentals

1. Cottage by the Castle – Downtown Spencer

Spencer

Sarah S.

￥41,986 total

includes taxes & fees

Aug 31 - Sep 1

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

Ware

Andrew

￥35,689 total

includes taxes & fees

Sep 22 - Sep 23

3. Clean & Cozy Private- 3 floor_R 4

Union HIll

￥18,248 total

includes taxes & fees

Aug 30 - Aug 31

4. Cozy Chic Countryside Haven - Sleeps 4 , Firepit

Sturbridge

Giora Y.

￥51,414 total

includes taxes & fees

Sep 22 - Sep 23

5. Angel Sky Challenge

Worcester

Cameron R.

￥41,725 total

includes taxes & fees

Aug 31 - Sep 1

6. Our pondside cabin - a charming retreat with modern amenities near Wachusett Mtn

Westminster

Shreya

￥82,781 total

includes taxes & fees

Sep 1 - Sep 2

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

Main South

"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...

Jeffrey B.

￥56,371 total

includes taxes & fees

Aug 30 - Aug 31

8. Newly Built Barn Loft in Pioneer Valley

Belchertown

Emily O.

￥34,259 total

includes taxes & fees

Aug 28 - Aug 29

9. Serene 1-bedroom suite on 75 acre horse property

Belchertown

"This was an amazing nightly rate for the region, and a lovely place to visit. I'm so glad we found it and was available! Brent and family take great care of the place, and it was so magical waking up and seeing horses just a few feet from the window. We had fun playing games under the gazebo while horses munched on hay. There's lots of good hiking in the area too. The suite had everything we needed like extra blankets, kitchen wares, games, and a great shower too. Highly recommended!"

Elizabeth

￥37,231 total

includes taxes & fees

Aug 31 - Sep 1

10. Dove Cabin up in the Trees

Holland

Maryann

￥41,480 total

includes taxes & fees

Sep 2 - Sep 3

11. Beautiful 2 Bedrooms with 2 Beds in Shrewsbury

Shrewsbury

Theresa L.

￥49,833 total

includes taxes & fees

Aug 31 - Sep 1

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

Westminster

Julianne R.

￥79,812 total

includes taxes & fees

Sep 7 - Sep 8

13. Newly Refreshed 3bd Spacious Unit Minutes from 290

Franklin Plantation

Anonymous traveler

￥40,087 total

includes taxes & fees

Sep 20 - Sep 21

14. Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8

Brimfield

Pamela L.

￥32,257 total

includes taxes & fees

Aug 31 - Sep 1

15. FREE Parking & Renovated 4BR Stay 1st-floor Apt Near Clark Uni, Laundry + AC 161

Worcester

Diane S.

￥70,949 total

includes taxes & fees

Sep 1 - Sep 2

16. 4-bedroom house in nice Holden with WiFi, AC

Holden

"The house was located in a quiet, nice, pleasant, neighborhood. The rooms were spacious and comfortable. The house was very clean and the beds were comfortable. The house was located near all kinds of stores, pharmacy’s, and good restaurants. I’d I had to make a negative comment it would be that all the bedrooms were on the second floor which was tough for two of our party. The property owner was quick to respond to questions we had. Overall, a very pleasant stay."

Samantha R.

￥90,364 total

includes taxes & fees

Sep 1 - Sep 2

17. Spacious 4-bedroom with four and half bathrooms

Worcester

Harmony F.

￥82,393 total

includes taxes & fees

Aug 30 - Aug 31

18. Heart of Shrewsbury St – 2BR Stay

Shrewsbury Street

Sharon

￥38,209 total

includes taxes & fees

Sep 8 - Sep 9

19. Clean & Cozy Private room - 3 floor_R 1

Union HIll

￥18,240 total

includes taxes & fees

Aug 31 - Sep 1

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Top Oakham Hotel Reviews

Hilton Garden Inn Worcester

10/10 Excellent

"The fact that there was a refrigerator and a microwave in the room where I didn’t have to go downstairs to heat up my food."

Scottish Inn Sturbridge

8/10 Good

"The approach to the property is very attractive with many vases of flowers. They are in the process of refreshing all the rooms, mine hadn't been done yet but it was acceptable. The water for the shower was hot which was very good. There ice machine broke but they brought mesome ice from another machine which was very thoughtful. I basically just slept there; I was in the area to visit 2 high school friends from 60+ years ago at the monastery at Spencer. The continental breakfast was basic compared to other hotels/motels that I've been at, but it was do able. Staff were very friendly and helpful. Again, the plantings around the front and side were a nice attraction to the motel. I would consider it on my next trip."

AC Hotel by Marriott Worcester

10/10 Excellent

"First time staying at the AC Worcester. The hotel has a trendy vibe with a modern look. We enjoyed the rainfall shower head, comfy bed and overall quiet rooms. They did have complimentary coffee, but not 24/7. We left at 5am hoping for a cup on the road, but it wasn’t available."

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?

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 Rock House Reservation. In the larger area, you’ll find Wachusett Mountain State 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.

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Check prices for these dates

Our top choices for Oakham vacation rentals

1. Cottage by the Castle – Downtown Spencer

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

3. Clean & Cozy Private- 3 floor_R 4

4. Cozy Chic Countryside Haven - Sleeps 4 , Firepit

5. Angel Sky Challenge

6. Our pondside cabin - a charming retreat with modern amenities near Wachusett Mtn

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

8. Newly Built Barn Loft in Pioneer Valley

9. Serene 1-bedroom suite on 75 acre horse property

10. Dove Cabin up in the Trees

11. Beautiful 2 Bedrooms with 2 Beds in Shrewsbury

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

13. Newly Refreshed 3bd Spacious Unit Minutes from 290

14. Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8

15. FREE Parking & Renovated 4BR Stay 1st-floor Apt Near Clark Uni, Laundry + AC 161

16. 4-bedroom house in nice Holden with WiFi, AC

17. Spacious 4-bedroom with four and half bathrooms

18. Heart of Shrewsbury St – 2BR Stay

19. Clean & Cozy Private room - 3 floor_R 1

Find vacation rentals that suit your style

Top Oakham Hotel Reviews

Hilton Garden Inn Worcester

Holiday Inn Express Hotel & Suites Auburn by IHG

Sturbridge Host Hotel & Conference Center

Scottish Inn Sturbridge

AC Hotel by Marriott Worcester

Wellsworth Hotel

Find out more about Oakham

Frequently asked questions

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