Oakham Vacation Rentals

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Check prices for these dates

Tonight
Jun 17 - Jun 18
Tomorrow
Jun 18 - Jun 19
This weekend
Jun 20 - Jun 22
Next weekend
Jun 27 - Jun 29

Vacation Rentals in Oakham

Home Away from Home!
Smart TV, fireplace

Home Away from Home!

10.0 out of 10, Exceptional, (5)
"Thank you for our little stay-cation! The property was beautiful and was exactly as expected. Plenty of rooms and bathrooms. My only wish was for more mirrors for us all to do our make up. But we made it work. "
The price is ￥26,797
￥56,723 total
includes taxes & fees
Jul 2 - Jul 3
Home Away from Home!
Beautiful two-story home close to downtown worcester 5beds-4bedroom
Fridge, microwave, oven, stovetop

Beautiful two-story home close to downtown worcester 5beds-4bedroom

8.6 out of 10, Excellent, (9)
"Great for our group while in town for work. Quiet neighbourhood. Close to town. "
The price is ￥31,375
￥62,229 total
includes taxes & fees
Jun 20 - Jun 21
Beautiful two-story home close to downtown worcester 5beds-4bedroom
Spacious 4-bedroom house in wonderful Worcester Area
Fridge, microwave, oven, stovetop

Spacious 4-bedroom house in wonderful Worcester Area

The price is ￥39,619
￥73,540 total
includes taxes & fees
Jun 25 - Jun 26
Spacious 4-bedroom house in wonderful Worcester Area
Dove Cabin up in the Trees
Exterior

Dove Cabin up in the Trees

10.0 out of 10, Exceptional, (11)
"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 ￥25,386
￥37,230 total
includes taxes & fees
Jun 18 - Jun 19
Dove Cabin up in the Trees
Convenient, clean and cozy 3 bedroom, 2 bath overlooking idyllic lake whittemore
Property grounds

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

10.0 out of 10, Exceptional, (187)
"The house is so clean has everything we need to host Christmas, beautiful lake view close to everything and owner is on site if you need anything "
Convenient, clean and cozy 3 bedroom, 2 bath overlooking idyllic lake whittemore
Beautiful Lakefront Home with Private Beach
Lake

Beautiful Lakefront Home with Private Beach

9.2 out of 10, Wonderful, (167)
"We had a great time staying at this property for a post-Christmas family celebration"
Beautiful Lakefront Home with Private Beach
Spacious 2 Bedroom 1 Bath apt
Private kitchen

Spacious 2 Bedroom 1 Bath apt

Spacious 2 Bedroom 1 Bath apt
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, (11)
"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 ￥25,212
￥33,198 total
includes taxes & fees
Jun 18 - Jun 19
Newly Built Barn Loft in Pioneer Valley
Spacious and luxurious 3-bedroom home w/jetted bathtub
Private kitchen

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
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, (12)
"We had a lovely stay! The house was spacious, clean, and comfortable. We appreciated being able to spread out or be together. The kitchen was also well appointed. Conveniently located near many points in Worcester. We would definitely stay again and recommend to others traveling to the area."
Spacious 4-bedroom house in charming Worcester with AC, WiFi
Trainmaster's Inn - Caboose
Private kitchen

Trainmaster's Inn - Caboose

9.2 out of 10, Wonderful, (5)
"A great stay in a vintage RR caboose. Thanks to everyone at Trainmasters Inn!"
The price is ￥21,611
￥46,029 total
includes taxes & fees
Jun 24 - Jun 25
Trainmaster's Inn - Caboose
Luxury Home, Pool, fireplace
Exterior

Luxury Home, Pool, fireplace

10.0 out of 10, Exceptional, (25)
"The property allowed for my extended family to gather under one roof and spend quality time together in a beautiful and quaint setting. "
Luxury Home, Pool, fireplace
Newly Refreshed 3bd Spacious Unit Minutes from 290
3 bedrooms, iron/ironing board, WiFi, bed sheets

Newly Refreshed 3bd Spacious Unit Minutes from 290

Newly Refreshed 3bd Spacious Unit Minutes from 290
One Bedroom Apartment with Separate Bunk Bed Area
TV

One Bedroom Apartment with Separate Bunk Bed Area

9.4 out of 10, Exceptional, (16)
"Nice property, very clean & well equipped. Perfect for me & my husband. Will definitely book again."
One Bedroom Apartment with Separate Bunk Bed Area
Lakefront; view of ski mountain, firepit, dock, kayaks, paddle board
Aerial view

Lakefront; view of ski mountain, firepit, dock, kayaks, paddle board

9.6 out of 10, Exceptional, (24)
"This was a very clean property. "
The price is ￥57,860
￥98,382 total
includes taxes & fees
Jun 22 - Jun 23
Lakefront; view of ski mountain, firepit, dock, kayaks, paddle board
Lake House in Sturbridge w/All the Views!
Outdoor spa tub

Lake House in Sturbridge w/All the Views!

9.6 out of 10, Exceptional, (14)
"This was a great visit and we so appreciate the host's consistent communication. The was accurately listed with a killer view of the lake and a hot tub for the ages. Communication is important when renting a house like this, and the host was a 10/10 in coordinating our new year's stay. Thank you so much!"
The price is ￥56,908
￥132,441 total
includes taxes & fees
Jun 18 - Jun 19
Lake House in Sturbridge w/All the Views!
Modern Mid-Century in Fitchburg
Fridge, microwave, oven, stovetop

Modern Mid-Century in Fitchburg

10.0 out of 10, Exceptional, (2)
"The home is beautifully renovated, very clean and comfortable. I would definitely stay here again next time I’m in town."
Modern Mid-Century in Fitchburg
1 Mi to Downtown & Palladium: Worcester Getaway!
Fridge, microwave, stovetop, dishwasher

1 Mi to Downtown & Palladium: Worcester Getaway!

10.0 out of 10, Exceptional, (2)
"We enjoyed our stay in this Condo when we came to the area for the Boston Marathon. It was clean and well supplied. It is in a quiet neighborhood and the beds are comfortable. We slept well. We definitely recommend this condo."
1 Mi to Downtown & Palladium: Worcester Getaway!
Lovely 3-bedroom City Escape
Property grounds

Lovely 3-bedroom City Escape

9.8 out of 10, Exceptional, (21)
"Our family gets together for Christmas and this home is the ideal place for part of the family to stay."
Lovely 3-bedroom City Escape
Beautiful 2 Bedrooms with 2 Beds in Shrewsbury
Fridge, microwave, oven, stovetop

Beautiful 2 Bedrooms with 2 Beds in Shrewsbury

9.8 out of 10, Exceptional, (35)
"The property is very cozy and clean.Excellent location we loved it. Thank you very much."
The price is ￥24,924
￥45,382 total
includes taxes & fees
Jun 21 - Jun 22
Beautiful 2 Bedrooms with 2 Beds in Shrewsbury
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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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 wonderful Worcester Area: This vacation home near Oakham is equipped with a garden, air-conditioning, and laundry facilities to help you feel comfortable during your stay. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

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.