Oakham Vacation Rentals

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Check prices for these dates

In two weeks
Feb 27 - Mar 1
In two months
Apr 10 - Apr 12
In three months
May 8 - May 10
In four months
Jun 5 - Jun 7

Our top choices for Oakham vacation rentals

Smart TV, fireplace

Home Away from Home!

Home Away from Home!
Worcester
9.4 out of 10, Exceptional, (15 reviews)
"Very clean ans spacious. Great communication "
United States
Tom K.
The price is ￥28,415
￥60,321 total
includes taxes & fees
Feb 14 - Feb 15
Home Away from Home!
Interior

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, (9 reviews)
"Nice place to stay a lot of family activities on the premises short distance to shopping and attractions"
United States
Andrew
The price is ￥21,426
￥25,876 total
includes taxes & fees
Feb 15 - Feb 16
Little House Inn - Private Home - Secluded - Ware - 2 bedroom, sleeps 6
Interior

Spacious Massachusetts Apartment #2

Spacious Massachusetts Apartment #2
West Brookfield
9.0 out of 10, Wonderful, (29 reviews)
"Really a cute place to stay, very clean and comfortable "
United States
Michelle J.
The price is ￥12,222
￥45,905 total
includes taxes & fees
Feb 16 - Feb 17
Spacious Massachusetts Apartment #2
Smart TV, books, stereo

Newly Built Barn Loft in Pioneer Valley

Newly Built Barn Loft in Pioneer Valley
Belchertown
9.4 out of 10, Exceptional, (23 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.
The price is ￥24,061
￥32,214 total
includes taxes & fees
Feb 16 - Feb 17
Newly Built Barn Loft in Pioneer Valley
Apartment, 2 Bedrooms | Interior

Cozy Adventure Filled Escape Free Parking 2 Bedroom Apts

Cozy Adventure Filled Escape Free Parking 2 Bedroom Apts
3.0 star property
Worcester
The price is ￥28,812
￥67,019 total
includes taxes & fees
Feb 14 - Feb 15
Cozy Adventure Filled Escape Free Parking 2 Bedroom Apts
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, (6 reviews)
"We needed a place to stay while our hardwood floors were being refinished and this was perfect. We have a dog and 2 cats and there was plenty of space. The house was clean and as advertised."
United States
Deb H.
The price is ￥42,012
￥77,982 total
includes taxes & fees
Feb 18 - Feb 19
Spacious 4-bedroom with four and half bathrooms
Fridge, microwave, oven, stovetop

Spacious & Clean 3BR APT near Clark University

Spacious & Clean 3BR APT near Clark University
Main South
10.0 out of 10, Exceptional, (1 review)
"Perfect apartment with lots of room; comfortable beds. Decorated with a personal touch (some VRBO's feel too impersonal) which made it very welcoming. Could not be better located for visiting Clark University campus!"
United States
Barb S.
The price is ￥19,936
￥34,706 total
includes taxes & fees
Feb 25 - Feb 26
Spacious & Clean 3BR APT near Clark University
Terrace/patio

Spacious Getaway by TreeHouse Brewery & Amazon WareHouse

Spacious Getaway by TreeHouse Brewery & Amazon WareHouse
Charlton
8.6 out of 10, Excellent, (24 reviews)
"It’s very clean with lots of room for the price. The neighborhood is quiet and peaceful. The pool is well-maintained. The owner is very responsive and helpful. Highly recommend!"
United States
Jan L.
The price is ￥75,621
￥144,039 total
includes taxes & fees
Mar 2 - Mar 3
Spacious Getaway by TreeHouse Brewery & Amazon WareHouse
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, (30 reviews)
"Great location. No easy access into water, must climb down wobbly stone wall. Bedding"
United States
Michael R.
Lakefront; view of ski mountain, firepit, dock, kayaks, paddle board
Books

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
The price is ￥24,061
￥30,630 total
includes taxes & fees
Feb 24 - Feb 25
Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8
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, (24 reviews)
"Our family stayed at the house for 2 nights to attend a nearby wedding. The house was just as pictured - lovely, clean, and perfect for our stay. The hosts have been very thoughtful about every detail from easy check-in to a well stocked kitchen to cozy blankets for the comfy couch. We had a wonderful time and highly recommend! "
United States
Kelly G.
The price is ￥48,123
￥95,528 total
includes taxes & fees
Feb 19 - Feb 20
Our pondside cabin - a charming retreat with modern amenities near Wachusett Mtn
Fridge, microwave, stovetop, coffee/tea maker

16/1 Worcester - Family Stay Close to Parks & Eats

16/1 Worcester - Family Stay Close to Parks & Eats
Worcester
The price is ￥19,002
￥52,968 total
includes taxes & fees
Feb 15 - Feb 16
16/1 Worcester - Family Stay Close to Parks & Eats
Dining

Warm & Cozy 4BR Near Airport + Winter-Ready Comfort• Fast WiFi

Warm & Cozy 4BR Near Airport + Winter-Ready Comfort• Fast WiFi
Webster Square
8.8 out of 10, Excellent, (3 reviews)
"Great house. Excellent back yard and privacy. "
United States
michael C.
The price is ￥29,790
￥89,868 total
includes taxes & fees
Feb 15 - Feb 16
Warm & Cozy 4BR Near Airport + Winter-Ready Comfort• Fast WiFi
Interior

4/1 - 3BR Worcester - Cozy Apartment Near Clark Uni

4/1 - 3BR Worcester - Cozy Apartment Near Clark Uni
Main South
The price is ￥16,255
￥44,655 total
includes taxes & fees
Feb 18 - Feb 19
4/1 - 3BR Worcester - Cozy Apartment Near Clark Uni
Dining

12B-Cozy 3BR Apartment with Koi Pond in Worcester

12B-Cozy 3BR Apartment with Koi Pond in Worcester
Millbury
The price is ￥18,180
￥49,412 total
includes taxes & fees
Feb 24 - Feb 25
12B-Cozy 3BR Apartment with Koi Pond in Worcester
Interior

Cozy Chic Countryside Haven - Sleeps 4 , Firepit

Cozy Chic Countryside Haven - Sleeps 4 , Firepit
Sturbridge
The price is ￥35,901
￥64,504 total
includes taxes & fees
Feb 14 - Feb 15
Cozy Chic Countryside Haven - Sleeps 4 , Firepit
Exterior

Beautifully updated home located just minutes from downtown Worcester.

Beautifully updated home located just minutes from downtown Worcester.
Worcester
10.0 out of 10, Exceptional, (1 review)
"Great clean place. Groceries and restaurants very close and convenient."
United States
Binoy K.
Beautifully updated home located just minutes from downtown Worcester.
Interior

Lake House in Sturbridge w/All the Views!

Lake House in Sturbridge w/All the Views!
Sturbridge
9.8 out of 10, Exceptional, (19 reviews)
"Thank you for a wonderful stay! Our family enjoyed the gorgeous views and the well-equipped home. There were toys, books, and games for the kids, and the beds were very comfortable. We’d definitely stay again!"
United States
Caitlin D.
The price is ￥61,296
￥147,402 total
includes taxes & fees
Feb 15 - Feb 16
Lake House in Sturbridge w/All the Views!
Interior

Electric House - Cozy Downtown stay

Electric House - Cozy Downtown stay
Canal District
4.0 out of 10, (1 review)
"It was uncomfortably cold and there was no running water. A refund would be in order."
United States
Deb P.
The price is ￥26,124
￥63,296 total
includes taxes & fees
Feb 14 - Feb 15
Electric House - Cozy Downtown stay
4 bedrooms, iron/ironing board, free WiFi, bed sheets

16/2 - 4BR Family Home in Worcester Near Parks

16/2 - 4BR Family Home in Worcester Near Parks
Worcester
The price is ￥19,002
￥52,266 total
includes taxes & fees
Feb 19 - Feb 20
16/2 - 4BR Family Home in Worcester Near Parks
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
"Beautiful and clean hotel and friendly staff"
Allison 1-night trip
Posted 2 days ago
Wellsworth Hotel

Find out more about Oakham

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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?

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 Green Hill Park, 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.