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Oakham Vacation Rentals

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

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
$259 nightly
The price is $261
Oct 12 - Oct 13
Total with taxes and fees
Cottage by the Castle – Downtown Spencer
A compact, modern laundry room with a built-in washer and dryer, a small storage cabinet, and a tiled floor.

2. 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.
$228 nightly
The price is $261
Oct 3 - Oct 4
Total with taxes and fees
Angel Sky Challenge
A grassy outdoor area with a hammock, chairs, and a stone wall.

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, (27 reviews)
"Nice place to stay a lot of family activities on the premises short distance to shopping and attractions"
United States
Andrew
$200 nightly
The price is $212
Oct 5 - Oct 6
Total with taxes and fees
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.

4. Clean & Cozy Private-3 floor_R 2

Clean & Cozy Private-3 floor_R 2
Union HIll
$100 nightly
The price is $115
Oct 5 - Oct 6
Total with taxes and fees
Clean & Cozy Private-3 floor_R 2
A modern kitchen with white cabinetry, a large island, and pendant lighting.

5. Modern Farmhouse Close to Mt. Wachusett

Modern Farmhouse Close to Mt. Wachusett
Holden
$610 nightly
The price is $644
Oct 7 - Oct 8
Total with taxes and fees
Modern Farmhouse Close to Mt. Wachusett
A modern kitchen with white cabinets, stainless steel appliances, and a central island with bar stools.

6. 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.
$534 nightly
The price is $564
Nov 1 - Nov 2
Total with taxes and fees
4-bedroom house in nice Holden with WiFi, AC
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
$496 nightly
The price is $544
Oct 22 - Oct 23
Total with taxes and fees
Our pondside cabin - a charming retreat with modern amenities near Wachusett Mtn
A modern kitchen with white cabinets, a stainless steel refrigerator, and a dining area with a table and chairs.

8. 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.
$342 nightly
The price is $382
Oct 18 - Oct 19
Total with taxes and fees
Cozy Chic Countryside Haven - Sleeps 4 , Firepit
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.
$317 nightly
The price is $363
Oct 4 - Oct 5
Total with taxes and fees
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.
$406 nightly
The price is $445
Oct 5 - Oct 6
Total with taxes and fees
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
$526 nightly
The price is $602
Oct 13 - Oct 14
Total with taxes and fees
Renovated Lakefront 5BR • Near Colleges • Sunsets • Sleeps 12
A living room with a TV, sofa, chairs, a lamp, and a window with sheer curtains.

12. Clean & Cozy Private- 3 floor_R 4

Clean & Cozy Private- 3 floor_R 4
Union HIll
$88 nightly
The price is $101
Oct 16 - Oct 17
Total with taxes and fees
Clean & Cozy Private- 3 floor_R 4
A living room with a TV, sofa, chairs, a lamp, and a window with sheer curtains.

13. Clean & Cozy Private- 3 floor_R 5

Clean & Cozy Private- 3 floor_R 5
Union HIll
2.0 out of 10, (1 review)
$100 nightly
The price is $115
Oct 5 - Oct 6
Total with taxes and fees
Clean & Cozy Private- 3 floor_R 5
A living room with two sofas, a coffee table, and a bookshelf.

14. 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
$210 nightly
The price is $240
Oct 6 - Oct 7
Total with taxes and fees
Heart of Shrewsbury St – 2BR Stay
A lakeside cabin with a dock, a boat, and a second-story deck.

15. 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.
$429 nightly
The price is $471
Oct 8 - Oct 9
Total with taxes and fees
Lakefront; view of ski mountain, firepit, dock, kayaks, laundry, outdoor shower
Living area

16. 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.
$391 nightly
The price is $448
Oct 5 - Oct 6
Total with taxes and fees
Newly Renovated 4BR Worcester Home • Pet-Friendly • Near I-290 & Park 16-2
A modern kitchen with a stainless steel refrigerator, double sink, and wooden flooring.

17. Spacious 4-bedroom with four and half bathrooms

Spacious 4-bedroom with four and half bathrooms
Worcester
9.8 out of 10, Exceptional, (22 reviews)
"Perfect location"
United States
Harmony F.
$449 nightly
The price is $514
Oct 4 - Oct 5
Total with taxes and fees
Spacious 4-bedroom with four and half bathrooms
A living room with a wooden staircase, a gray sectional sofa, a colorful rug, and a ceiling fan.

18. Spacious 5-bedroom home with three full bathrooms in charming Worcester location

Spacious 5-bedroom home with three full bathrooms in charming Worcester location
Worcester
$435 nightly
The price is $498
Oct 4 - Oct 5
Total with taxes and fees
Spacious 5-bedroom home with three full bathrooms in charming Worcester location
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.

19. 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.
$201 nightly
The price is $212
Oct 4 - Oct 5
Total with taxes and fees
Newly Built Barn Loft in Pioneer Valley
A wooden gazebo with a metal roof, surrounded by a brick patio with outdoor seating.

20. 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.
$246 nightly
The price is $260
Oct 28 - Oct 29
Total with taxes and fees
Serene 1-bedroom suite on 75 acre horse property
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

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 $115 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.

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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.