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Oakham Vacation Rentals

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Check prices for these dates

In two weeks
Jun 26 - Jun 28
In two months
Aug 7 - Aug 9
In three months
Sep 4 - Sep 6
In four months
Oct 2 - Oct 4

Our top choices for Oakham vacation rentals

Bathroom

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

Beautiful & Cozy 2 BR/ 2Beds/ Netflix/Alexa/Roku.
Shrewsbury
9.6 out of 10, Exceptional, (32 reviews)
"Lovely and great location "
United States
Kimberlee K.
$274 nightly
The price is $306
Jun 15 - Jun 16
Total with taxes and fees
Beautiful & Cozy 2 BR/ 2Beds/ Netflix/Alexa/Roku.
Exterior

Dove Cabin up in the Trees

Dove Cabin up in the Trees
Holland
9.8 out of 10, Exceptional, (31 reviews)
"So calm, clean and relaxing, and beautiful! Wonderful stay! "
United States
Sarah G.
$244 nightly
The price is $257
Jun 15 - Jun 16
Total with taxes and fees
Dove Cabin up in the Trees
Interior

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.
$308 nightly
The price is $344
Jun 15 - Jun 16
Total with taxes and fees
Trainmaster's Inn - Caboose
Smart TV

Beautiful 2 Bedrooms with 2 Beds in Shrewsbury

Beautiful 2 Bedrooms with 2 Beds in Shrewsbury
Shrewsbury
9.6 out of 10, Exceptional, (47 reviews)
"Amazing host and fabulous spacious property. "
United States
Kelly L.
$303 nightly
The price is $338
Jun 22 - Jun 23
Total with taxes and fees
Beautiful 2 Bedrooms with 2 Beds in Shrewsbury
Property grounds

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, (13 reviews)
"Nice place to stay a lot of family activities on the premises short distance to shopping and attractions"
United States
Andrew
$203 nightly
The price is $215
Jun 17 - Jun 18
Total with taxes and fees
Little House Inn - Private Home - Secluded - Ware - 2 bedroom, sleeps 6
Interior

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.
$224 nightly
The price is $256
Jun 15 - Jun 16
Total with taxes and fees
Angel Sky Challenge
Smart TV

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, (29 reviews)
"Very pleasant stay. Would definitely stay here again. "
United States
Shreya
$496 nightly
The price is $544
Jun 30 - Jul 1
Total with taxes and fees
Our pondside cabin - a charming retreat with modern amenities near Wachusett Mtn
Property grounds

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, (5 reviews)
"This is a nice place for solo travelers or a small family with kids. The kid’s bedroom has tons of games and is themed nicely. The backyard is huge but unfenced and the property is off of a busy road. Th house itself was clean and the host offered a variety of things such as slippers for the whole family, house shoes, and bath things for everyone. The house does not have a tv but the wifi works well. "
United States
Chantay-Rose
$229 nightly
The price is $256
Jun 22 - Jun 23
Total with taxes and fees
Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8
Smart TV

Mid-Century Comfort & Style

Mid-Century Comfort & Style
Fitchburg
9.6 out of 10, Exceptional, (11 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
$415 nightly
The price is $442
Jun 15 - Jun 16
Total with taxes and fees
Mid-Century Comfort & Style
Interior

Charming 1-bedroom apartment with AC & Breakfast in Sturbridge

Charming 1-bedroom apartment with AC & Breakfast in Sturbridge
Sturbridge
$134 nightly
The price is $150
Jun 28 - Jun 29
Total with taxes and fees
Charming 1-bedroom apartment with AC & Breakfast in Sturbridge
Apartment (3 Bedrooms) | Interior

1 Mi to Downtown & Palladium: Worcester Getaway!

1 Mi to Downtown & Palladium: Worcester Getaway!
3.0 star property
Worcester
10.0 out of 10, Exceptional, (1 review)
"The place was amazing, just needed a few updates and repairs, but nothing that made our stay bad or inconvenient. "
United States
Michelle
$427 nightly
The price is $489
Jun 20 - Jun 21
Total with taxes and fees
1 Mi to Downtown & Palladium: Worcester Getaway!
Outdoor dining

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, (28 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.
$233 nightly
The price is $246
Jun 17 - Jun 18
Total with taxes and fees
Serene 1-bedroom suite on 75 acre horse property
Interior

Cozy 3-bedroom house in serene Worcester with fitness room and office

Cozy 3-bedroom house in serene Worcester with fitness room and office
Worcester
10.0 out of 10, Exceptional, (1 review)
"The only thing missing was a BBQ"
United States
Charmen B.
$309 nightly
The price is $354
Jun 23 - Jun 24
Total with taxes and fees
Cozy 3-bedroom house in serene Worcester with fitness room and office
Dining

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, (1 review)
"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.
$386 nightly
The price is $442
Jul 8 - Jul 9
Total with taxes and fees
Beautiful Worcester Downtown King Bd/Office World Cup Boston
Smart TV, books, stereo

Newly Built Barn Loft in Pioneer Valley

Newly Built Barn Loft in Pioneer Valley
Belchertown
9.6 out of 10, Exceptional, (28 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.
$202 nightly
The price is $213
Jun 15 - Jun 16
Total with taxes and fees
Newly Built Barn Loft in Pioneer Valley
Exterior

Modern 3BR Near FSU • 15 Min to Wachusett

Modern 3BR Near FSU • 15 Min to Wachusett
Fitchburg
10.0 out of 10, Exceptional, (15 reviews)
"House was amazing, great people to work with! "
United States
Keith
$515 nightly
The price is $549
Jun 29 - Jun 30
Total with taxes and fees
Modern 3BR Near FSU • 15 Min to Wachusett
Exterior

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, (37 reviews)
"Cutest home! My family loved it! "
United States
Shanna D.
$507 nightly
The price is $556
Jun 18 - Jun 19
Total with taxes and fees
Lakefront; view of ski mountain, firepit, dock, kayaks, paddle board
Interior

Cozy Chic Countryside Haven - Sleeps 4 , Firepit

Cozy Chic Countryside Haven - Sleeps 4 , Firepit
Sturbridge
10.0 out of 10, Exceptional, (1 review)
"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
Jun 15 - Jun 16
Total with taxes and fees
Cozy Chic Countryside Haven - Sleeps 4 , Firepit
Fridge, microwave, oven, stovetop

Spacious 4-bedroom with four and half bathrooms

Spacious 4-bedroom with four and half bathrooms
Worcester
10.0 out of 10, Exceptional, (12 reviews)
"10/10 great place to stay"
United States
Tyler B.
$445 nightly
The price is $509
Jun 17 - Jun 18
Total with taxes and fees
Spacious 4-bedroom with four and half bathrooms
TV

Large 3BD 1st Floor Apartment Minutes from 290

Large 3BD 1st Floor Apartment Minutes from 290
Franklin Plantation
10.0 out of 10, Exceptional, (3 reviews)
"It was a great place for my family and i"
United States
Taisha M.
$240 nightly
The price is $275
Jul 5 - Jul 6
Total with taxes and fees
Large 3BD 1st Floor Apartment Minutes from 290
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
"Quiet historic Inn and town. Love sitting on balcony to appreciate the birds, Revolutionary Cemetery and ancient trees. In town Enrico's Brick Oven has delicious gourmet pizza and icy cold Sangria. Inn provides delicious coffee and fresh baked pastries. Only comment is, pet fee is a reasonable $25 but the pet room; altho clean and quiet, in sore need of upgrade in bathroom and floor carpet. We've stayed here 4x a year for over 20 years and love the ambiance and character."
Jean 1-night trip
Posted 5 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 $213 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?

Direct waterfront Lake House, stunning views Sleeps 8 on a private PENINSULA!: This vacation home near Oakham is located on a lake and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 3 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 private yard and a selection of games.

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.