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Oakham Vacation Rentals

Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Oakham vacation rentals

A wooden cabin bedroom with a bed, a nightstand, a lamp, and a bunk bed.

1. The Christmas Cottage, 4BR New England Escape

The Christmas Cottage, 4BR New England Escape
Rutland
$700 nightly
The price is $740
Nov 12 - Nov 13
Total with taxes and fees
The Christmas Cottage, 4BR New England Escape
The Cottage is nestled next to the historic Sagendorph Mansion.

2. Cottage by the Castle – Downtown Spencer

Cottage by the Castle – Downtown Spencer
Spencer
10.0 out of 10, Exceptional, (9 reviews)
"Nice, clean and well maintained. Would stay here again."
United States
Sarah S.
$222 nightly
The price is $223
Nov 12 - Nov 13
Total with taxes and fees
Cottage by the Castle – Downtown Spencer
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
9.6 out of 10, Exceptional, (28 reviews)
"This was a super cozy ,cute place to stay . Host had muffins , juice and milk for us. The property was quiet and very peaceful."
United States
theresa H.
$165 nightly
The price is $174
Nov 12 - Nov 13
Total with taxes and fees
Little House Inn - Private Home - Secluded - Ware - 2 bedroom, sleeps 6
A bedroom with a large bed, a vanity with a mirror, a window with blinds, and a potted plant.

4. 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, (3 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.
$614 nightly
The price is $649
Nov 22 - Nov 23
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.

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, (40 reviews)
"Very pleasant stay. Would definitely stay here again. "
United States
Shreya
$447 nightly
The price is $490
Nov 16 - Nov 17
Total with taxes and fees
Our pondside cabin - a charming retreat with modern amenities near Wachusett Mtn
Two Adirondack chairs on a wooden deck with a view of a lake and trees.

6. Worcester Lakefront Cottage Apt w/ Shared Dock!

Worcester Lakefront Cottage Apt w/ Shared Dock!
3.0 star property
Worcester
$395 nightly
The price is $452
Nov 22 - Nov 23
Total with taxes and fees
Worcester Lakefront Cottage Apt w/ Shared Dock!
A living room with a TV, sofa, chairs, a lamp, and a window with sheer curtains.

7. 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
$92 nightly
The price is $105
Nov 15 - Nov 16
Total with taxes and fees
Clean & Cozy Private-3 floor_R 2
A compact, modern laundry room with a built-in washer and dryer, a small storage cabinet, and a tiled floor.

8. 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.
$216 nightly
The price is $247
Nov 12 - Nov 13
Total with taxes and fees
Angel Sky Challenge
A modern kitchen with white cabinets, a stainless steel refrigerator, and a dining area with a table and chairs.

9. Cozy Chic Countryside Haven - Sleeps 4 , Firepit

Cozy Chic Countryside Haven - Sleeps 4 , Firepit
Sturbridge
10.0 out of 10, Exceptional, (4 reviews)
"Gorgeously decorated and ultra-clean. Was the perfect rental for my sisters wedding at Salem Cross Inn"
United States
Trish N.
$327 nightly
The price is $365
Nov 12 - Nov 13
Total with taxes and fees
Cozy Chic Countryside Haven - Sleeps 4 , Firepit
A modern kitchen with a stainless steel refrigerator, double sink, and wooden flooring.

10. 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)
"Great, clean location to stay."
United States
Mike O.
$428 nightly
The price is $490
Nov 16 - Nov 17
Total with taxes and fees
Spacious 4-bedroom with four and half bathrooms
Living area

11. 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.
$276 nightly
The price is $316
Nov 12 - Nov 13
Total with taxes and fees
Newly Renovated 4BR Worcester Home • Pet-Friendly • Near I-290 & Park 16-2
Two Adirondack chairs on a wooden deck with a view of a lake and trees.

12. Worcester Lakefront Cottage Apt w/ Shared Dock!

Worcester Lakefront Cottage Apt w/ Shared Dock!
Worcester
9.4 out of 10, Exceptional, (20 reviews)
"The host was very accommodating and responsive. Great property in a great location, would stay again!"
United States
Michaela H.
$385 nightly
The price is $441
Nov 22 - Nov 23
Total with taxes and fees
Worcester Lakefront Cottage Apt w/ Shared Dock!
A living room with a gray sofa, a coffee table, and a rug. There are two windows with blinds, a door, and a wall-mounted plant.

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

Large 3BD 1st Floor Apartment Minutes from 290
Franklin Plantation
10.0 out of 10, Exceptional, (5 reviews)
"It was a great place for my family and i"
United States
Taisha M.
$210 nightly
The price is $240
Nov 12 - Nov 13
Total with taxes and fees
Large 3BD 1st Floor Apartment Minutes from 290
A room with two black leather sofas, a glass-top coffee table, white walls, and a ceiling light.

14. 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
8.8 out of 10, Excellent, (3 reviews)
"Rented the property to attend a series of events at Clark University. Literally walking distance to the school so it was quite convenient. Apartment was clean, beds were comfortable. Being able to park three cars in the driveway was a huge plus as street parking near the apartment was extremely challenging. Being a Clark alum, was quite familiar with the neighborhood so I knew what to expect. Felt completely safe in the apartment as every door to the hallways had sufficient locks. We did blow a...
United States
Elyse D.
$289 nightly
The price is $331
Nov 15 - Nov 16
Total with taxes and fees
Modern Stay 3BR Worcester Apt • FREE Parking near Clark University & I-290 4/1
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.

15. Newly Built Barn Loft in Pioneer Valley

Newly Built Barn Loft in Pioneer Valley
Belchertown
9.6 out of 10, Exceptional, (39 reviews)
"Great place for a couple to stay. Hostess was fantastic. We had everything we needed. Would definitely recommend and would stay again!"
United States
Doreen R.
$216 nightly
The price is $228
Nov 12 - Nov 13
Total with taxes and fees
Newly Built Barn Loft in Pioneer Valley
A living room with two sofas, a coffee table, and a bookshelf.

16. 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
$200 nightly
The price is $228
Nov 17 - Nov 18
Total with taxes and fees
Heart of Shrewsbury St – 2BR Stay
A wooden fence with a rustic appearance, surrounded by lush greenery and purple flowers.

17. Two Bedroom Guesthouse near many attractions pet friendly with private deck

Two Bedroom Guesthouse near many attractions pet friendly with private deck
Gardner
10.0 out of 10, Exceptional, (3 reviews)
"Cute little guesthouse. Super clean and lovely decorated."
United States
Kristin R.
$276 nightly
The price is $308
Dec 7 - Dec 8
Total with taxes and fees
Two Bedroom Guesthouse near many attractions pet friendly with private deck
A wooden cabin with a glass upper floor, surrounded by a forest.

18. Dove Cabin up in the Trees

Dove Cabin up in the Trees
Holland
9.8 out of 10, Exceptional, (39 reviews)
"Excellent location for a quiet and relaxing getaway. The cabin was clean and well outfitted. Our host greeted us, talked about the history of the property, kayaking around the lake was great, such a good idea for an old youth camp with so much potential. We’ll definitely be returning for another stay"
United States
Zachary C.
$233 nightly
The price is $246
Nov 12 - Nov 13
Total with taxes and fees
Dove Cabin up in the Trees
A neatly made bed with rolled towels, a bedside table with a lamp, and a large mirror on the wall.

19. 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
$210 nightly
The price is $240
Nov 12 - Nov 13
Total with taxes and fees
Newly Refreshed 3bd Spacious Unit Minutes from 290
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, (40 reviews)
"We had a great, restorative stay in Liberty Woods. It is a lovely oasis with kind humans, friendly animals and beautiful horses in a beautiful setting."
United States
Anna O.
$244 nightly
The price is $258
Nov 30 - Dec 1
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

The Colonial Hotel

The Colonial Hotel

8/10 Good
"loved the restaurant."
Greg 1-night trip
Posted 3 hours ago
The Colonial 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 $105 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.