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Oakham Vacation Rentals

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Check prices for these dates

In two weeks
Aug 14 - Aug 16
In two months
Sep 25 - Sep 27
In three months
Oct 23 - Oct 25
In four months
Nov 20 - Nov 22

Our top choices for Oakham vacation rentals

Exterior

1. 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.
$233 nightly
The price is $235
Aug 2 - Aug 3
Total with taxes and fees
Cottage by the Castle – Downtown Spencer
Living area

2. Clean & Cozy Private- 3 floor_R 4

Clean & Cozy Private- 3 floor_R 4
Union HIll
$88 nightly
The price is $101
Aug 2 - Aug 3
Total with taxes and fees
Clean & Cozy Private- 3 floor_R 4
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
$233 nightly
The price is $246
Aug 10 - Aug 11
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.
$226 nightly
The price is $259
Aug 1 - Aug 2
Total with taxes and fees
Angel Sky Challenge
3 bedrooms, WiFi

5. 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
$216 nightly
The price is $247
Aug 2 - Aug 3
Total with taxes and fees
Newly Refreshed 3bd Spacious Unit Minutes from 290
Dining

6. 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.
$305 nightly
The price is $349
Aug 17 - Aug 18
Total with taxes and fees
Beautiful Worcester Downtown King Bd/Office World Cup Boston
Smart TV

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, (34 reviews)
"Very pleasant stay. Would definitely stay here again. "
United States
Shreya
$478 nightly
The price is $524
Aug 5 - Aug 6
Total with taxes and fees
Our pondside cabin - a charming retreat with modern amenities near Wachusett Mtn
Interior

8. 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)
$318 nightly
The price is $364
Aug 4 - Aug 5
Total with taxes and fees
Modern Stay 3BR Worcester Apt • FREE Parking near Clark University & I-290 4/1
TV

9. 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.
$216 nightly
The price is $247
Aug 2 - Aug 3
Total with taxes and fees
Large 3BD 1st Floor Apartment Minutes from 290
Smart TV, books, stereo

10. Newly Built Barn Loft in Pioneer Valley

Newly Built Barn Loft in Pioneer Valley
Belchertown
9.6 out of 10, Exceptional, (33 reviews)
"Kitchen was clean and well stocked with water, and some small snacks. "
United States
Cheyenne K.
$202 nightly
The price is $213
Aug 7 - Aug 8
Total with taxes and fees
Newly Built Barn Loft in Pioneer Valley
Exterior

11. Dove Cabin up in the Trees

Dove Cabin up in the Trees
Holland
9.8 out of 10, Exceptional, (32 reviews)
"Sue is a great host, making necessary adjustments to suit the circumstances, generous and flexible. The dove cabin is so sweet, comfortable beds, cozy stove and fully equipped kitchen. And lovely porch! There’s a really cool swing on the way down to a peaceful pond!"
United States
kathryn m.
$243 nightly
The price is $256
Aug 2 - Aug 3
Total with taxes and fees
Dove Cabin up in the Trees
Exterior

12. 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, (39 reviews)
"Cutest home! My family loved it! "
United States
Shanna D.
$500 nightly
The price is $549
Aug 2 - Aug 3
Total with taxes and fees
Lakefront; view of ski mountain, firepit, dock, kayaks, paddle board
Interior

13. 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.
$310 nightly
The price is $346
Aug 2 - Aug 3
Total with taxes and fees
Trainmaster's Inn - Caboose
Outdoor dining

14. 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, (32 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.
$240 nightly
The price is $254
Aug 18 - Aug 19
Total with taxes and fees
Serene 1-bedroom suite on 75 acre horse property
Apartment, 2 Bedrooms | Interior

15. Cozy Adventure Filled Escape Free Parking 2 Bedroom Apts

Cozy Adventure Filled Escape Free Parking 2 Bedroom Apts
3.0 star property
Worcester
$399 nightly
The price is $457
Aug 18 - Aug 19
Total with taxes and fees
Cozy Adventure Filled Escape Free Parking 2 Bedroom Apts
Coffee/tea maker, fridge, microwave, oven

16. Spacious 4-bedroom with four and half bathrooms

Spacious 4-bedroom with four and half bathrooms
Worcester
10.0 out of 10, Exceptional, (15 reviews)
"Perfect location"
United States
Harmony F.
$449 nightly
The price is $514
Aug 8 - Aug 9
Total with taxes and fees
Spacious 4-bedroom with four and half bathrooms
Smart TV, books

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
$241 nightly
The price is $275
Aug 3 - Aug 4
Total with taxes and fees
Heart of Shrewsbury St – 2BR Stay
Smart TV

18. 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.
$376 nightly
The price is $430
Aug 3 - Aug 4
Total with taxes and fees
Newly Renovated 4BR Worcester Home • Pet-Friendly • Near I-290 & Park 16-2
Private kitchen

19. 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, (1 review)
"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."
United States
Samantha R.
$537 nightly
The price is $568
Aug 23 - Aug 24
Total with taxes and fees
4-bedroom house in nice Holden with WiFi, AC
Interior

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

Charming 1-bedroom apartment with AC & Breakfast in Sturbridge
Sturbridge
$129 nightly
The price is $144
Aug 7 - Aug 8
Total with taxes and fees
Charming 1-bedroom apartment with AC & Breakfast in Sturbridge
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
"Everything about this place and our stay was fantastic! Super friendly staff & evening manager is very engaging. Dinner & drinks in the restaurant was top notch. Highly recommend!"
Laurie 1-night trip
Posted 9 hours ago
Wellsworth Hotel

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 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.