Oakham Vacation Rentals

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Check prices for these dates

In two weeks
Sep 12 - Sep 14
In one month
Sep 26 - Sep 28
In two months
Oct 24 - Oct 26
In three months
Nov 21 - Nov 23

Vacation Rentals in Oakham

Our top choices for Oakham vacation rentals

Dove Cabin up in the Trees
Exterior

Dove Cabin up in the Trees

9.8 out of 10, Exceptional, (19)
"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 ￥25,877
￥37,950 total
includes taxes & fees
Aug 28 - Aug 29
Dove Cabin up in the Trees
Spacious 4-bedroom house in charming Worcester with AC, WiFi
Fridge, microwave, oven, stovetop

Spacious 4-bedroom house in charming Worcester with AC, WiFi

2.0 star property
10.0 out of 10, Exceptional, (17)
"Our stay at this property was great. Very clean and spacious. Area was very accessible to main roads. Our hosts were very responsive from booking through to the end of our stay. Will look to stay next time we visit Worcester "
Spacious 4-bedroom house in charming Worcester with AC, WiFi
Beautiful Lakefront Home with Private Beach
Lake

Beautiful Lakefront Home with Private Beach

9.2 out of 10, Wonderful, (174)
"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
Close to Colleges: Worcester Apt w/ Lake Access!
Cookware/dishes/utensils

Close to Colleges: Worcester Apt w/ Lake Access!

10.0 out of 10, Exceptional, (10)
"This is a super clean spacious apartment. Comfortable and convenient to restaurants and shopping. Host was very attentive to any questions or problems. Highly recommended! "
Close to Colleges: Worcester Apt w/ Lake Access!
Newly Built Barn Loft in Pioneer Valley
Smart TV, books, stereo

Newly Built Barn Loft in Pioneer Valley

2.0 star property
9.4 out of 10, Exceptional, (15)
"Small but well maintained, clean, well stocked & nic"
The price is ￥23,223
￥31,716 total
includes taxes & fees
Sep 1 - Sep 2
Newly Built Barn Loft in Pioneer Valley
Modern Mid-Century in Fitchburg
Fridge, microwave, oven, stovetop

Modern Mid-Century in Fitchburg

9.8 out of 10, Exceptional, (6)
"Great property close to where we needed to be."
Modern Mid-Century in Fitchburg
Luxury Home, Pool, fireplace
Exterior

Luxury Home, Pool, fireplace

10.0 out of 10, Exceptional, (29)
"A truly beautiful place with the most gorgeous pool and landscaping. We will be back for sure!"
Luxury Home, Pool, fireplace
Hillside Hideaway: full family home, 250 ft from the lake shore. Dog friendly!
Exterior

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 ￥42,671
￥82,509 total
includes taxes & fees
Sep 10 - Sep 11
Hillside Hideaway: full family home, 250 ft from the lake shore. Dog friendly!
Serene 1-bedroom suite on 65 acre horse property
Fridge, microwave, oven, stovetop

Serene 1-bedroom suite on 65 acre horse property

10.0 out of 10, Exceptional, (21)
"Had such a wonderful stay at this space. Brent was very communicative about the check in/check out process which was greatly appreciated. The main living room area is very spacious and the bedroom was comfortable. I would definitely stay here again in the future!"
The price is ￥19,242
￥36,703 total
includes taxes & fees
Sep 1 - Sep 2
Serene 1-bedroom suite on 65 acre horse property
Worcester Home on Indian Lake w/ Shared Boat Dock!
TV

Worcester Home on Indian Lake w/ Shared Boat Dock!

9.8 out of 10, Exceptional, (22)
"If you are looking for a great place to stay while in the Worcester area family this place will fill your need. The peaceful view on the lake is amazing."
Worcester Home on Indian Lake w/ Shared Boat Dock!
3 Bed / 1.5 Bath Townhome
Fridge, microwave, oven, stovetop

3 Bed / 1.5 Bath Townhome

9.2 out of 10, Wonderful, (16)
"You will hear a little road noice but other then that it was perfect! Extremely clean and a great location. Highly recommend "
3 Bed / 1.5 Bath Townhome
Lakefront: Fish, Kayak, Canoe, Near Treehouse Brewery, Sturbridge Village!
Outdoor dining

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

10.0 out of 10, Exceptional, (2)
"Great little cottage at a lake. Super well appointed with pots, pans, gas grill, etc.... great hosts very attentive! "
Lakefront: Fish, Kayak, Canoe, Near Treehouse Brewery, Sturbridge Village!
Bright Charming/Netflix/Roku
Interior

Bright Charming/Netflix/Roku

2.0 star property
The price is ￥23,621
￥82,387 total
includes taxes & fees
Sep 8 - Sep 9
Bright Charming/Netflix/Roku
Brimfield Waterfront cottage
Property grounds

Brimfield Waterfront cottage

10.0 out of 10, Exceptional, (6)
"Property is in excellent condition, just the right amount of space for us. "
Brimfield Waterfront cottage
Spacious 4-bedroom with four and half bathrooms
Fridge, microwave, oven, stovetop

Spacious 4-bedroom with four and half bathrooms

10.0 out of 10, Exceptional, (2)
"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 ￥40,549
￥75,266 total
includes taxes & fees
Aug 31 - Sep 1
Spacious 4-bedroom with four and half bathrooms
Home Away from Home!
Smart TV, fireplace

Home Away from Home!

9.2 out of 10, Wonderful, (12)
"Lots of bedrooms with a great family gathering space. Quiet neighborhood. Would stay again at this property. Nicely decorated. "
The price is ￥27,426
￥58,728 total
includes taxes & fees
Sep 7 - Sep 8
Home Away from Home!
Direct waterfront Lake House, stunning views Sleeps 8 on a private PENINSULA!
Terrace/patio

Direct waterfront Lake House, stunning views Sleeps 8 on a private PENINSULA!

9.8 out of 10, Exceptional, (87)
"We enjoyed our stay. As a family of cooks the kitchen was very small and this was a bit of a challenge. It is a very relaxing cottage and we enjoyed the water even if it was a bit cold as our time was in April. I would certainly return to this rental. It is very clean and the sun room was wonderful."
Direct waterfront Lake House, stunning views Sleeps 8 on a private PENINSULA!
Lake House in Sturbridge w/All the Views!
Outdoor spa tub

Lake House in Sturbridge w/All the Views!

9.8 out of 10, Exceptional, (17)
"Loved the windows and light in the house. Quiet and peaceful. "
The price is ￥92,894
￥178,095 total
includes taxes & fees
Sep 1 - Sep 2
Lake House in Sturbridge w/All the Views!
Trainmaster's Inn - Caboose
Private kitchen

Trainmaster's Inn - Caboose

9.6 out of 10, Exceptional, (8)
"A great stay in a vintage RR caboose. Thanks to everyone at Trainmasters Inn!"
The price is ￥22,118
￥48,317 total
includes taxes & fees
Aug 31 - Sep 1
Trainmaster's Inn - Caboose
Spacious & Clean 3BR APT near Clark University
Fridge, microwave, oven, stovetop

Spacious & Clean 3BR APT near Clark University

The price is ￥40,549
￥61,258 total
includes taxes & fees
Sep 8 - Sep 9
Spacious & Clean 3BR APT near Clark University
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

Find out more about Oakham

Find out more about Oakham

Search for holiday rentals in Oakham on Expedia! You can easily find your home rentals, villas, holiday apartments in Oakham using one of the methods below:

  • View our selection of featured holiday rentals in Oakham
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Look no further and take a look at our great range of rental properties in 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?

Spacious 4-bedroom house in charming Worcester with AC, WiFi: This vacation home rental near Oakham offers a patio, a garden, and air-conditioning to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like 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 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.