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Oakham Vacation Rentals

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Oakham vacation rentals

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
$226 nightly
The price is $227
Sep 28 - Sep 29
Total with taxes and fees
Cottage by the Castle – Downtown Spencer
A living room with a TV, sofa, chairs, a lamp, and a window with sheer curtains.

2. Clean & Cozy Private-3 floor_R 2

Clean & Cozy Private-3 floor_R 2
Union HIll
$100 nightly
The price is $115
Sep 27 - Sep 28
Total with taxes and fees
Clean & Cozy Private-3 floor_R 2
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, (26 reviews)
"Nice place to stay a lot of family activities on the premises short distance to shopping and attractions"
United States
Andrew
$204 nightly
The price is $216
Oct 27 - Oct 28
Total with taxes and fees
Little House Inn - Private Home - Secluded - Ware - 2 bedroom, sleeps 6
A modern kitchen with white cabinetry, a large island, and pendant lighting.

4. Modern Farmhouse Close to Mt. Wachusett

Modern Farmhouse Close to Mt. Wachusett
Holden
$572 nightly
The price is $604
Oct 7 - Oct 8
Total with taxes and fees
Modern Farmhouse Close to Mt. Wachusett
A modern kitchen with white cabinets, a stainless steel refrigerator, and a dining area with a table and chairs.

5. 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.
$270 nightly
The price is $302
Sep 30 - Oct 1
Total with taxes and fees
Cozy Chic Countryside Haven - Sleeps 4 , Firepit
A room with a blue wall, a mirror, a table with chairs, potted plants, and a Christmas tree.

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

Charming 1-bedroom apartment with AC & Breakfast in Sturbridge
Sturbridge
$164 nightly
The price is $183
Oct 4 - Oct 5
Total with taxes and fees
Charming 1-bedroom apartment with AC & Breakfast in Sturbridge
A compact, modern laundry room with a built-in washer and dryer, a small storage cabinet, and a tiled floor.

7. 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.
$220 nightly
The price is $252
Sep 27 - Sep 28
Total with taxes and fees
Angel Sky Challenge
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.

8. 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.
$198 nightly
The price is $209
Sep 27 - Sep 28
Total with taxes and fees
Newly Built Barn Loft in Pioneer Valley
A house with a stone wall and a dock extending into a calm body of water.

9. 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.
$385 nightly
The price is $422
Sep 28 - Sep 29
Total with taxes and fees
Lakefront; view of ski mountain, firepit, dock, kayaks, paddle board
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.

10. 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.
$232 nightly
The price is $266
Sep 28 - Sep 29
Total with taxes and fees
Large 3BD 1st Floor Apartment Minutes from 290
A wooden cabin with a glass upper floor, surrounded by a forest.

11. Dove Cabin up in the Trees

Dove Cabin up in the Trees
Holland
9.8 out of 10, Exceptional, (36 reviews)
"The owner was pleasant and accommodating "
United States
Maryann
$236 nightly
The price is $249
Sep 27 - Sep 28
Total with taxes and fees
Dove Cabin up in the Trees
A room with two black leather sofas, a glass-top coffee table, white walls, and a ceiling light.

12. 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.
$278 nightly
The price is $318
Sep 27 - Sep 28
Total with taxes and fees
Modern Stay 3BR Worcester Apt • FREE Parking near Clark University & I-290 4/1
A bedroom with a large mirror, a bed with floral bedding, a standing lamp, and a window with curtains.

13. Beautiful & Cozy 2 BR/ 2Beds/ Netflix/Alexa/Roku.

Beautiful & Cozy 2 BR/ 2Beds/ Netflix/Alexa/Roku.
Shrewsbury
9.6 out of 10, Exceptional, (37 reviews)
"Lovely and great location "
United States
Kimberlee K.
Beautiful & Cozy 2 BR/ 2Beds/ Netflix/Alexa/Roku.
A spacious living room with a wooden ceiling, a grey sofa, a staircase, and a large window.

14. 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
$443 nightly
The price is $486
Sep 28 - Sep 29
Total with taxes and fees
Our pondside cabin - a charming retreat with modern amenities near Wachusett Mtn
A living room with two sofas, a coffee table, and a bookshelf.

15. 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
$204 nightly
The price is $233
Sep 29 - Sep 30
Total with taxes and fees
Heart of Shrewsbury St – 2BR Stay
A modern kitchen with a marble countertop, stainless steel sink, and a dining area with a green sofa and a plant.

16. Fitchburg quiet side modern 2BD.

Fitchburg quiet side modern 2BD.
Fitchburg
9.8 out of 10, Exceptional, (7 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
$253 nightly
The price is $270
Oct 5 - Oct 6
Total with taxes and fees
Fitchburg quiet side modern 2BD.
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
10.0 out of 10, Exceptional, (21 reviews)
"Perfect location"
United States
Harmony F.
$421 nightly
The price is $482
Sep 27 - Sep 28
Total with taxes and fees
Spacious 4-bedroom with four and half bathrooms

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.
$319 nightly
The price is $365
Sep 27 - Sep 28
Total with taxes and fees
Newly Renovated 4BR Worcester Home • Pet-Friendly • Near I-290 & Park 16-2
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
$215 nightly
The price is $246
Sep 30 - Oct 1
Total with taxes and fees
Newly Refreshed 3bd Spacious Unit Minutes from 290
A living room with a sofa, a clock, a floor lamp, and a rug.

20. Beautiful 2 Bedrooms with 2 Beds in Shrewsbury

Beautiful 2 Bedrooms with 2 Beds in Shrewsbury
Shrewsbury
9.4 out of 10, Exceptional, (54 reviews)
"Amazing host and fabulous spacious property. "
United States
Kelly L.
$256 nightly
The price is $286
Oct 13 - Oct 14
Total with taxes and fees
Beautiful 2 Bedrooms with 2 Beds in Shrewsbury
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

Hilton Garden Inn Worcester

Hilton Garden Inn Worcester

10/10 Excellent
"Everyone was super nice super helpful. It was a great experience."
Joshua 5-night trip
Posted 7 hours ago
Hilton Garden Inn Worcester

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 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.