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Oakham Vacation Rentals

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Check prices for these dates

In two weeks
Aug 28 - Aug 30
In two months
Oct 9 - Oct 11
In three months
Nov 6 - Nov 8
In four months
Dec 4 - Dec 6

Our top choices for Oakham vacation rentals

Living area

1. Clean & Cozy Private- 3 floor_R 4

Clean & Cozy Private- 3 floor_R 4
Union HIll
$100 nightly
The price is $115
Aug 17 - Aug 18
Total with taxes and fees
Clean & Cozy Private- 3 floor_R 4
Exterior

2. Cottage by the Castle – Downtown Spencer

Cottage by the Castle – Downtown Spencer
Spencer
10.0 out of 10, Exceptional, (3 reviews)
"Nice, clean and well maintained. Would stay here again."
United States
Sarah S.
$262 nightly
The price is $264
Aug 17 - Aug 18
Total with taxes and fees
Cottage by the Castle – Downtown Spencer
Property grounds

3. 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, (21 reviews)
"Nice place to stay a lot of family activities on the premises short distance to shopping and attractions"
United States
Andrew
$208 nightly
The price is $220
Aug 17 - Aug 18
Total with taxes and fees
Little House Inn - Private Home - Secluded - Ware - 2 bedroom, sleeps 6
Interior

4. 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.
$229 nightly
The price is $262
Aug 17 - Aug 18
Total with taxes and fees
Angel Sky Challenge
Smart TV

5. 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, (36 reviews)
"Very pleasant stay. Would definitely stay here again. "
United States
Shreya
$474 nightly
The price is $520
Aug 17 - Aug 18
Total with taxes and fees
Our pondside cabin - a charming retreat with modern amenities near Wachusett Mtn
Outdoor dining

6. 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, (33 reviews)
"Clean rooms, pleasant and relaxing atmosphere. Nothing lacking in amenities. Friendly hosts and communication very good. Would stay again and highly recommend!"
United States
Donald M.
$221 nightly
The price is $234
Aug 31 - Sep 1
Total with taxes and fees
Serene 1-bedroom suite on 75 acre horse property
TV

7. Large 3BD 1st Floor Apartment Minutes from 290

Large 3BD 1st Floor Apartment Minutes from 290
Franklin Plantation
10.0 out of 10, Exceptional, (4 reviews)
"It was a great place for my family and i"
United States
Taisha M.
$257 nightly
The price is $294
Aug 19 - Aug 20
Total with taxes and fees
Large 3BD 1st Floor Apartment Minutes from 290
Exterior

8. Dove Cabin up in the Trees

Dove Cabin up in the Trees
Holland
9.6 out of 10, Exceptional, (34 reviews)
"So calm, clean and relaxing, and beautiful! Wonderful stay! "
United States
Sarah G.
$247 nightly
The price is $261
Aug 17 - Aug 18
Total with taxes and fees
Dove Cabin up in the Trees
Interior

9. Modern 1-bedroom apartment in peaceful Sturbridge with AC

Modern 1-bedroom apartment in peaceful Sturbridge with AC
Sturbridge
8.0 out of 10, Very Good, (1 review)
"Clean place short drive to all Sturbridge attractions."
United States
Lynn M. T.
$79 nightly
The price is $88
Aug 17 - Aug 18
Total with taxes and fees
Modern 1-bedroom apartment in peaceful Sturbridge with AC
Exterior

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, (41 reviews)
"Beautiful location and perfect for a fishing getaway! House was clean and cozy!"
United States
Julianne R.
$457 nightly
The price is $501
Sep 7 - Sep 8
Total with taxes and fees
Lakefront; view of ski mountain, firepit, dock, kayaks, paddle board
Interior

11. 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
10.0 out of 10, Exceptional, (1 review)
$320 nightly
The price is $367
Aug 17 - Aug 18
Total with taxes and fees
Modern Stay 3BR Worcester Apt • FREE Parking near Clark University & I-290 4/1
Smart TV

12. 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.
$356 nightly
The price is $407
Aug 17 - Aug 18
Total with taxes and fees
Newly Renovated 4BR Worcester Home • Pet-Friendly • Near I-290 & Park 16-2
Smart TV, books, stereo

13. Newly Built Barn Loft in Pioneer Valley

Newly Built Barn Loft in Pioneer Valley
Belchertown
9.6 out of 10, Exceptional, (34 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.
$203 nightly
The price is $214
Aug 23 - Aug 24
Total with taxes and fees
Newly Built Barn Loft in Pioneer Valley
Interior

14. 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.
$347 nightly
The price is $388
Sep 15 - Sep 16
Total with taxes and fees
Cozy Chic Countryside Haven - Sleeps 4 , Firepit
1 bedroom, internet, bed sheets

15. Clean & Cozy Private room - 3 floor_R 1

Clean & Cozy Private room - 3 floor_R 1
Union HIll
2.0 out of 10, (1 review)
$100 nightly
The price is $115
Aug 23 - Aug 24
Total with taxes and fees
Clean & Cozy Private room - 3 floor_R 1
Property grounds

16. 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.
$171 nightly
The price is $191
Aug 18 - Aug 19
Total with taxes and fees
Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8
Interior

17. Fitchburg quiet side modern 2BD.

Fitchburg quiet side modern 2BD.
Fitchburg
9.8 out of 10, Exceptional, (6 reviews)
"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
$317 nightly
The price is $338
Sep 13 - Sep 14
Total with taxes and fees
Fitchburg quiet side modern 2BD.
Smart TV

18. Mid-Century Comfort & Style

Mid-Century Comfort & Style
Fitchburg
9.6 out of 10, Exceptional, (14 reviews)
"What a great place! Very clean, and comfortable. Several very good local restaurants within walking distance. Can’t say enough good things to say. Next time we are in the area, this will be our first pick for a place to stay."
United States
Robert
Mid-Century Comfort & Style
Apartment, 2 Bedrooms | Interior

19. Cozy Adventure Filled Escape Free Parking 2 Bedroom Apts

Cozy Adventure Filled Escape Free Parking 2 Bedroom Apts
3.0 star property
Worcester
$390 nightly
The price is $446
Aug 18 - Aug 19
Total with taxes and fees
Cozy Adventure Filled Escape Free Parking 2 Bedroom Apts
Smart TV, books

20. 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
$243 nightly
The price is $278
Aug 17 - Aug 18
Total with taxes and fees
Heart of Shrewsbury St – 2BR Stay
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

8/10 Good
"The facility was very nice. We ate in the on site tavern/restaurant. One problem is there was a fire alarm malfunction before 7am. We had to vacate our room. The fire company was summoned. The alarm was malfunctioning…They got it turned off. We returned to our room but the alarm went off again. We left our room and it was turned off again. There was an electrical issue that had to be addressed by an electrician. We checked out. They were busy so we did not get any compensation for the disruption"
MaryAnna 1-night trip
Posted 10 hours ago
Publick House Historic Inn and Country Motor Lodge

Find out more about Oakham

Everything you need to know about Oakham vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Oakham vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Oakham vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Oakham vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Oakham. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Oakham in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $88 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Oakham rentals

At Expedia, we put the best Oakham vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Oakham rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Oakham vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Oakham. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

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.