Oakham Holiday Rentals

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Holiday Rentals in Oakham

Serene 1-bedroom suite on 65 acre horse property

10.0 out of 10, Exceptional, (10)
"The hosts were responsive and wonderful. The setting is beautiful. A peaceful retreat among the trees, with the horses as neighbors. "
Serene 1-bedroom suite on 65 acre horse property

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

9.6 out of 10, Exceptional, (18)
"This was a very clean property. "
The price is AU$607
includes taxes & fees
16 Jan - 17 Jan
Lakefront; view of ski mountain, firepit, dock, kayaks, paddle board

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

9.0 out of 10, Wonderful, (4)
"Everything as advertised and very responsive to one question about the WiFi our first night. "
The price is AU$821
includes taxes & fees
11 Feb - 12 Feb
Beautiful two-story home close to downtown worcester 5beds-4bedroom

Spacious Massachusetts Apartment #2

9.4 out of 10, Exceptional, (16)
"using me to have to wash it before returning it to the Hertz office. Definitely would stay there again when traveling to visit my sisters."
Spacious Massachusetts Apartment #2

Relaxing Retreat

9.8 out of 10, Exceptional, (26)
"Very nice place to stay. We enjoyed the games available in the closet. The grandson enjoyed the weight and treadmill area. "
Relaxing Retreat

Holiday Lake House near Treehouse Brewery & Amazon Warehouse with King Beds

9.0 out of 10, Wonderful, (8)
"We loved this cottage! It's right on Glen Echo Lake in Charlton, perfect for a romantic getaway. The cottage was spacious and the king sized bed was wonderfully comfortable. The bathroom has two sinks and two shower heads. The furniture was all comfortable and clean. There's a smart TV so you can get all your streaming services and YouTube. The living room couch power reclines and is dangerously comfortable. Everything looked new and modern. The kitchen comes with all the essentials: pots and...
Holiday Lake House near Treehouse Brewery & Amazon Warehouse with King Beds

Cottage on Partridge Pond

10.0 out of 10, Exceptional, (17)
"This cute cottage served our family of 5 adults. It was clean and well decorated. Would definitely recommend. "
Cottage on Partridge Pond

Quiet and Cozy Campground Cabin near the lake

9.4 out of 10, Exceptional, (3)
"Cute and cozy cabin with friendly staff, close to everything"
Quiet and Cozy Campground Cabin near the lake

Cozy 2-Floor Apartment with Garage Access

9.6 out of 10, Exceptional, (17)
"There was a small issue but the host handled the situation very quickly highly recommend this property. We will use again."
Cozy 2-Floor Apartment with Garage Access

Leicester Lake Front Home, Come Relax!

10.0 out of 10, Exceptional, (24)
"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!

Lake House in Sturbridge w/All the Views!

9.4 out of 10, Exceptional, (10)
"The house worked perfectly for a weekend getaway for four old friends looking for a chance to relax and catch up. Great for hanging out, time by the fire pit, and meandering walks. We were disappointed that the hot tub wasn’t working the weekend we were there but the owner was very responsive, getting two different technicians to come look at it and giving us a partial refund because it couldn’t be fixed in time. We’d love to come back in warmer weather and be able to take advantage of the water...
The price is AU$1,519
includes taxes & fees
12 Jan - 13 Jan
Lake House in Sturbridge w/All the Views!

5 bedrooms Home away from Home

10.0 out of 10, Exceptional, (10)
"This house was lovely. Very Clean, big enough for our entire family and that everyone had their own space, beds were very comfy, and it was on a quiet street. This house is perfect for family gatherings. Will hope to be back in the future!"
5 bedrooms Home away from Home

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

10.0 out of 10, Exceptional, (14)
"We had such a great stay here! The owner has created a cute, clean, and organized place. It is well decorated and very comfortable. It easily accommodated our family of four adults, plus some friends who came for dinner. The owner was also very responsive when we needed help with anything. Highly recommend it!!"
The price is AU$1,063
includes taxes & fees
22 Jan - 23 Jan
Our pondside cabin - a charming retreat with modern amenities near Wachusett Mtn

Worcester Home on Indian Lake w/ Shared Boat Dock!

9.6 out of 10, Exceptional, (10)
"The bedroom and bath on the living floor was great for my 88 year old mother. Beautiful lake view and walks. "
Worcester Home on Indian Lake w/ Shared Boat Dock!

Beautiful 2 Bedrooms with 2 Beds in Shrewsbury

9.8 out of 10, Exceptional, (33)
"This was an amazing property! My mother stayed there and said it was cozy and she felt at home. The place was clean, cozy, and quaint! Would definitely stay there again!"
Beautiful 2 Bedrooms with 2 Beds in Shrewsbury

Fall Villa near Treehouse Brewery & Amazon Warehouse with King Beds

8.4 out of 10, Very good, (21)
"It was nice. Not really waterfront. Pool was nice on a hot day. FYI- Google maps took us to the wrong house. Glad the neighbor didn't mind us at the door at 10 p.m. Plenty of room for family gathering."
Fall Villa near Treehouse Brewery & Amazon Warehouse with King Beds

Luxury Home, Pool, fireplace

10.0 out of 10, Exceptional, (23)
"The property allowed for my extended family to gather under one roof and spend quality time together in a beautiful and quaint setting. "
The price is AU$2,967
includes taxes & fees
16 Jan - 17 Jan
Luxury Home, Pool, fireplace

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

9.8 out of 10, Exceptional, (83)
"We were in Sturbridge for a wedding and wanted a place to enjoy the spectacular of a fall weekend in MA, this place had spectacular views and was clean to stay at"
Direct waterfront Lake House, stunning views Sleeps 8 on a private PENINSULA!

Spacious luxury 3 bedroom apartment

8.0 out of 10, Very good, (2)
"Came from out of town with friends to enjoy a music festival at the Palladium. Location was easy to find and accesible to shops/food. Apartment was easy to access around back side. In our case we walked up the driveway as the gate was locked. Safe second floor apartment. Bed were clean, and rooms spacious. Only thing that was inconvenient the missing handle from the freezer door. "
Spacious luxury 3 bedroom apartment

Trainmaster's Inn - Caboose

9.4 out of 10, Exceptional, (3)
"Husband is a railfan he was at the tracks several times a day"
The price is AU$525
includes taxes & fees
13 Jan - 14 Jan
Trainmaster's Inn - Caboose
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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Other types of properties in Oakham you may be interested in

Great Wolf Lodge Boston / Fitchburg, MA

3.5 star property
8.6 out of 10, Excellent, (862)
"Impressed with water park and little stores like the magic quest. Arcade is SOOOO EXPENSIVE. should’ve just bought a $200 package when I got there."
The price is AU$385
includes taxes & fees
16 Jan - 17 Jan
Great Wolf Lodge Boston / Fitchburg, MA

Wellsworth Hotel

3.0 star property
9.2 out of 10, Wonderful, (1043)
"great staff and rooms, restaurant is also wonderful! "
The price is AU$169
includes taxes & fees
23 Jan - 24 Jan
Wellsworth Hotel

AC Hotel by Marriott Worcester

3.5 star property
9.2 out of 10, Wonderful, (1002)
"Convenient "
The price is AU$281
includes taxes & fees
19 Jan - 20 Jan
AC Hotel by Marriott Worcester
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.

Frequently asked questions

Are there holiday rentals in Oakham?

Yes, there are holiday rentals close to the most popular sights in Oakham, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Oakham has to offer?

Holiday Lake House near Treehouse Brewery & Amazon Warehouse with King Beds: This holiday home rental outside of Oakham offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a selection of games and 1 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 wider area, you’ll find Hardwick Vineyard and Winery and Wachusett Mountain State Reservation.

What’s a holiday rental in Oakham like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Oakham. Holiday rentals feature extras like WiFi and washers and dryers to help you enjoy your stay. If you're concerned about a clean environment, a holiday rental can offer a sense of security away from public hotel lifts and bustling concierge desks while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great choice for family gatherings.