Oakham Vacation Rentals

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Check prices for these dates

In two weeks
Apr 17 - Apr 19
In two months
May 29 - May 31
In three months
Jun 26 - Jun 28
In four months
Jul 24 - Jul 26

Our top choices for Oakham vacation rentals

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, (27 reviews)
"Great family spot. Very clean and comfortable. Convenient to local attractions and shopping. "
United States
Dennyse M.
The price is ￥35,957
￥82,046 total
includes taxes & fees
Apr 1 - Apr 2
Our pondside cabin - a charming retreat with modern amenities near Wachusett Mtn
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)
"Cutest home! My family loved it! "
United States
Shanna D.
The price is ￥23,972
￥69,249 total
includes taxes & fees
Apr 12 - Apr 13
Lakefront; view of ski mountain, firepit, dock, kayaks, paddle board
Interior

Little House Inn - Private Home - Secluded - Ware - 2 bedroom, sleeps 6

Little House Inn - Private Home - Secluded - Ware - 2 bedroom, sleeps 6
Ware
9.6 out of 10, Exceptional, (10 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 ￥26,369
￥31,251 total
includes taxes & fees
Apr 6 - Apr 7
Little House Inn - Private Home - Secluded - Ware - 2 bedroom, sleeps 6
Smart TV, fireplace

Home Away from Home!

Home Away from Home!
Worcester
9.4 out of 10, Exceptional, (17 reviews)
"Very clean ans spacious. Great communication "
United States
Tom K.
The price is ￥29,725
￥63,101 total
includes taxes & fees
Apr 6 - Apr 7
Home Away from Home!
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 ￥71,195
￥140,626 total
includes taxes & fees
Apr 1 - Apr 2
Spacious Getaway by TreeHouse Brewery & Amazon WareHouse
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, (9 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 ￥43,948
￥81,209 total
includes taxes & fees
Apr 1 - Apr 2
Spacious 4-bedroom with four and half bathrooms
Exterior

Dove Cabin up in the Trees

Dove Cabin up in the Trees
Holland
9.8 out of 10, Exceptional, (27 reviews)
"So calm, clean and relaxing, and beautiful! Wonderful stay! "
United States
Sarah G.
The price is ￥31,163
￥44,088 total
includes taxes & fees
Apr 18 - Apr 19
Dove Cabin up in the Trees
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 ￥23,908
￥30,276 total
includes taxes & fees
Apr 1 - Apr 2
Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8
Smart TV, books

Heart of Shrewsbury St – 2BR Stay

Heart of Shrewsbury St – 2BR Stay
Shrewsbury Street
The price is ￥33,800
￥44,173 total
includes taxes & fees
Apr 6 - Apr 7
Heart of Shrewsbury St – 2BR Stay
2 bedrooms, iron/ironing board, internet, bed sheets

Beautiful Worcester Downtown King Bd/Office World Cup Boston

Beautiful Worcester Downtown King Bd/Office World Cup Boston
Worcester
The price is ￥17,259
￥46,640 total
includes taxes & fees
Apr 8 - Apr 9
Beautiful Worcester Downtown King Bd/Office World Cup Boston
Apartment, 2 Bedrooms | Living area | Smart TV, streaming services

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 ￥26,222
￥64,319 total
includes taxes & fees
Apr 14 - Apr 15
Cozy Adventure Filled Escape Free Parking 2 Bedroom Apts
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 ￥11,506
￥46,412 total
includes taxes & fees
Apr 2 - Apr 3
Spacious Massachusetts Apartment #2
Dining

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

12B-Cozy 3BR Apartment with Koi Pond in Worcester
Millbury
10.0 out of 10, Exceptional, (1 review)
"Super nice place to stay with lots of food options in the area."
United States
Roberto A G.
The price is ￥33,081
￥67,737 total
includes taxes & fees
Apr 1 - Apr 2
12B-Cozy 3BR Apartment with Koi Pond in Worcester
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, (25 reviews)
"Welcoming comfortable and quiet"
United States
Catherine R.
The price is ￥26,369
￥45,102 total
includes taxes & fees
Apr 20 - Apr 21
Serene 1-bedroom suite on 75 acre horse property
4 bedrooms, iron/ironing board, free WiFi, bed sheets

Spacious 4BR Family Home in Worcester near Parks 16/2

Spacious 4BR Family Home in Worcester near Parks 16/2
Worcester
10.0 out of 10, Exceptional, (1 review)
"Our stay was great! The home was beautiful and well kept. Plenty of room for a group of us to stay comfortably. The host was fantastic and very attentive. Overall, it was exactly what we were looking for. Would highly recommend."
United States
Kristen S.
The price is ￥21,734
￥56,700 total
includes taxes & fees
Apr 1 - Apr 2
Spacious 4BR Family Home in Worcester near Parks 16/2
Smart TV, fireplace

SalsVista 1st Floor Corner Apt

SalsVista 1st Floor Corner Apt
Forest Grove
9.8 out of 10, Exceptional, (7 reviews)
"Check in was easy. Kitchen was adequate. Plenty of wine openers. Highly recommend. "
United States
Christopher M.
The price is ￥32,761
￥76,271 total
includes taxes & fees
Apr 6 - Apr 7
SalsVista 1st Floor Corner Apt
Interior

Cozy Chic Countryside Haven - Sleeps 4 , Firepit

Cozy Chic Countryside Haven - Sleeps 4 , Firepit
Sturbridge
The price is ￥37,555
￥67,834 total
includes taxes & fees
Apr 1 - Apr 2
Cozy Chic Countryside Haven - Sleeps 4 , Firepit
Interior

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

4/1 - 3BR Worcester - Cozy Apartment Near Clark Uni
Main South
The price is ￥28,888
￥60,767 total
includes taxes & fees
Apr 7 - Apr 8
4/1 - 3BR Worcester - Cozy Apartment Near Clark Uni
Interior

Lake House in Sturbridge w/All the Views!

Lake House in Sturbridge w/All the Views!
Sturbridge
9.6 out of 10, Exceptional, (20 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 ￥49,696
￥137,043 total
includes taxes & fees
Apr 1 - Apr 2
Lake House in Sturbridge w/All the Views!
Interior

NEW! Cozy Adventure Filled Escape Free parking

NEW! Cozy Adventure Filled Escape Free parking
Worcester
The price is ￥28,616
￥64,776 total
includes taxes & fees
Apr 1 - Apr 2
NEW! Cozy Adventure Filled Escape Free parking
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

Great Wolf Lodge Boston / Fitchburg, MA

Great Wolf Lodge Boston / Fitchburg, MA

10/10 Excellent
"Amazing "
Arianna 2-night trip
Posted 1 hour ago
Great Wolf Lodge Boston / Fitchburg, MA

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 EcoTarium, 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.