Oakham Vacation Rentals

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Check prices for these dates

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Aug 2 - Aug 3
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Aug 3 - Aug 4
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Aug 8 - Aug 10
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Aug 15 - Aug 17

Vacation Rentals in Oakham

Dove Cabin up in the Trees
Escape to a serene forest retreat with a cozy cabin featuring a gabled roof and inviting front porch.

Dove Cabin up in the Trees

10.0 out of 10, Exceptional, (16)
"This is the sweetest property to stay in when visiting Brimfield market. I highly suggest any of the cabins on the property "
The price is ￥25,869
￥37,938 total
includes taxes & fees
Aug 3 - Aug 4
Dove Cabin up in the Trees
Beautiful Lakefront Home with Private Beach
Surrounded by vibrant autumn colors, this serene lakeside setting offers a peaceful escape.

Beautiful Lakefront Home with Private Beach

9.2 out of 10, Wonderful, (171)
"Beautiful house and grounds! Very private with lots of room along with homey touches. Kids loved the toy cabinet and the pool table. Easy access to Boston. We thoroughly enjoyed our Easter weekend there! "
Beautiful Lakefront Home with Private Beach
Beautiful & Historic Cottage, Steps to Elm Park
Relax on the outdoor deck with a bench and chair, surrounded by lush greenery and a view of the interior.

Beautiful & Historic Cottage, Steps to Elm Park

2.5 star property
10.0 out of 10, Exceptional, (11)
"place was very nice and owners where very responsive, and you can't beat the location. great restaurants a few blocks away.I been looking for a place to stay when I come visit my sister and this might be it."
Beautiful & Historic Cottage, Steps to Elm Park
Newly Built Barn Loft in Pioneer Valley
Relax in this spacious living area with a kitchen, dining, and seating space, featuring a large mirror and a TV.

Newly Built Barn Loft in Pioneer Valley

2.0 star property
9.4 out of 10, Exceptional, (14)
"This was a sweet place to stay while we were in the area for a graduation. It is a beautiful little apartment with everything we needed, cozy and quiet, and Lucienne’s communications were clear and welcoming!"
The price is ￥23,216
￥31,551 total
includes taxes & fees
Aug 5 - Aug 6
Newly Built Barn Loft in Pioneer Valley
Modern Mid-Century in Fitchburg
Enjoy cooking in this well-equipped kitchen with a microwave, oven, and dishwasher.

Modern Mid-Century in Fitchburg

10.0 out of 10, Exceptional, (5)
"Great property close to where we needed to be."
Modern Mid-Century in Fitchburg
Spacious Private Retreat Near Holyoke State Park!
Enjoy meals in the kitchen with a dining area featuring a table and chairs.

Spacious Private Retreat Near Holyoke State Park!

10.0 out of 10, Exceptional, (9)
"We stayed for a guys hunting trip and the place was what we needed after a long day"
Spacious Private Retreat Near Holyoke State Park!
Spacious 4-bedroom with four and half bathrooms
Enjoy a view of the surrounding area from the large window in this kitchen, featuring a double sink and sleek appliances.

Spacious 4-bedroom with four and half bathrooms

10.0 out of 10, Exceptional, (1)
"We had room for each of the adults, which included adult children. At these ages they no longer want to share a bed or bathroom with anyone. Perfect that we could come together, but have our own separate spaces. Very clean and comfortable with everything you need."
The price is ￥40,535
￥75,240 total
includes taxes & fees
Aug 3 - Aug 4
Spacious 4-bedroom with four and half bathrooms
Beautiful & Cozy 2 BR/ 2Beds/ Netflix/Alexa/Roku.
Explore the playground with a slide, climbing areas, and a platform featuring a circular window, set amidst a natural surroundings.

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

9.6 out of 10, Exceptional, (23)
"Love this place. Quiet and has everything you need to feel welcome. Thank you to Eben the host as he is always on top of things"
Beautiful & Cozy 2 BR/ 2Beds/ Netflix/Alexa/Roku.
Lakefront: Fish, Kayak, Canoe, Near Treehouse Brewery, Sturbridge Village!
Outdoor dining

Lakefront: Fish, Kayak, Canoe, Near Treehouse Brewery, Sturbridge Village!

Lakefront: Fish, Kayak, Canoe, Near Treehouse Brewery, Sturbridge Village!
Beautiful Renovated Townhome w/parking
Step out onto the covered porch, flanked by a railing and street view, and enjoy the serene atmosphere.

Beautiful Renovated Townhome w/parking

9.4 out of 10, Exceptional, (14)
"Great communication, assistance with maintenance, and receptive to feedback. Would stay again . "
Beautiful Renovated Townhome w/parking
Charming 3-bedroom apartment in historic Grafton with WiFi
Compact kitchen with stainless steel appliances, oven, and gas stove, featuring white cabinetry and a tiled backsplash.

Charming 3-bedroom apartment in historic Grafton with WiFi

9.8 out of 10, Exceptional, (10)
"We appreciated the communication and space we had! Neighborhood was quiet and host gave amazing recommendations. "
Charming 3-bedroom apartment in historic Grafton with WiFi
Brand new 3 bedroom house in welcoming Worcester with WiFi and AC
Enjoy cooking in this well-equipped kitchen with stainless steel appliances and a central island.

Brand new 3 bedroom house in welcoming Worcester with WiFi and AC

9.0 out of 10, Wonderful, (2)
"House was new, bright, and clean. "
Brand new 3 bedroom house in welcoming Worcester with WiFi and AC
Convenient, clean and cozy 3 bedroom, 2 bath overlooking idyllic lake whittemore
Hammock suspended between trees, offering a serene spot to relax by the water.

Convenient, clean and cozy 3 bedroom, 2 bath overlooking idyllic lake whittemore

10.0 out of 10, Exceptional, (189)
"This was our third time staying, and definately won’t be our last!"
Convenient, clean and cozy 3 bedroom, 2 bath overlooking idyllic lake whittemore
Our pondside cabin - a charming retreat with modern amenities near Wachusett Mtn
Relax in this cozy cabin-style room with a comfortable sofa, coffee table, and large window offering a view of the outdoors.

Our pondside cabin - a charming retreat with modern amenities near Wachusett Mtn

10.0 out of 10, Exceptional, (20)
"Kathleen was an amazing host and the property exceeded our expectations. The kids loved the bunk room and loft and the surrounding area provided something for all interests. We will definitely be planning another stay. "
The price is ￥36,850
￥80,849 total
includes taxes & fees
Aug 26 - Aug 27
Our pondside cabin - a charming retreat with modern amenities near Wachusett Mtn
Wachusett Mountain Getaway, Lake Adjacent Home! Near 1761 Old Mill and Trails!
Snow and ski sports

Wachusett Mountain Getaway, Lake Adjacent Home! Near 1761 Old Mill and Trails!

9.8 out of 10, Exceptional, (87)
"My family stayed here while in town for a family wedding. The house was very spacious and well stocked. Location was convenient for our events in Westminster. "
Wachusett Mountain Getaway, Lake Adjacent Home! Near 1761 Old Mill and Trails!
Leicester Lake Front Home, Come Relax!
Enjoy al fresco dining on the deck overlooking the water, where a barbecue grill and comfortable seating await.

Leicester Lake Front Home, Come Relax!

10.0 out of 10, Exceptional, (26)
"Great family time and comfortable house to spend time with family during a visit to see our daughter at Holy Cross! "
Leicester Lake Front Home, Come Relax!
Hillside Hideaway: full family home, 250 ft from the lake shore. Dog friendly!
Relax on the covered porch, surrounded by a peaceful lawn and mature trees.

Hillside Hideaway: full family home, 250 ft from the lake shore. Dog friendly!

9.8 out of 10, Exceptional, (10)
"Property is in excellent condition and well appointed. We enjoyed our stay."
The price is ￥49,785
￥91,661 total
includes taxes & fees
Aug 27 - Aug 28
Hillside Hideaway: full family home, 250 ft from the lake shore. Dog friendly!
Close to Colleges: Worcester Apt w/ Lake Access!
Apartment (1 Bedroom) | Interior

Close to Colleges: Worcester Apt w/ Lake Access!

3.0 star property
8.0 out of 10, Very Good, (1)
"Cozy place. Noises from upstairs in the middle of the night. "
Close to Colleges: Worcester Apt w/ Lake Access!
Spacious & Clean 3BR APT near Clark University
Modern kitchen with a coffee maker and microwave, featuring a welcome sign and natural light.

Spacious & Clean 3BR APT near Clark University

The price is ￥40,535
￥61,237 total
includes taxes & fees
Aug 11 - Aug 12
Spacious & Clean 3BR APT near Clark University
Spacious and luxurious 3-bedroom home w/jetted bathtub
Enjoy cooking in this well-equipped kitchen with a refrigerator, microwave, and dark cabinetry.

Spacious and luxurious 3-bedroom home w/jetted bathtub

9.2 out of 10, Wonderful, (5)
"Only caveats are the air conditioning is primitive"
Spacious and luxurious 3-bedroom home w/jetted bathtub
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

Beechwood Hotel

Beechwood Hotel

10/10 Excellent
"Excellent stay as usual "
Ginige 5-night trip
Posted 18 hours ago
Beechwood Hotel

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?

Beautiful Lakefront Home with Private Beach: This vacation home rental 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 dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of games.

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 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.