Holiday Rentals in Oakham

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Holiday Rentals in Oakham

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

9.4 out of 10, Exceptional, (16)
"Place was pristine, great location on the lake. Beautiful scenery with the mountains, used the kayaks to get around the lake and catch some fish! My son and i caught pickerel, perch, bass, crappies, and pumkinseeds. Quick drive from Boston @ a little over a hour."
Lakefront; view of ski mountain, firepit, dock, kayaks, paddle board

Beautiful 2 Bedrooms with 2 Beds in Shrewsbury

9.8 out of 10, Exceptional, (29)
"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

One Bedroom Fully Furnished Apartment

9.8 out of 10, Exceptional, (11)
"The apartment is nice and just as pictured, and we had a comfortable stay. What's not clear from the listing is that it isn't in a residential neighborhood but in the middle of a shopping center. That wasn't really a problem for us, but it was a little surprising."
One Bedroom Fully Furnished Apartment

Lakefront; view of ski mountain, firepit, dock, kayaks, laundry, outdoor shower

10.0 out of 10, Exceptional, (12)
"We had a great time. The house was very nice and clean. The lake was really lovely for boating and swimming."
Lakefront; view of ski mountain, firepit, dock, kayaks, laundry, outdoor shower

Cozy 2-Floor Apartment with Garage Access

9.4 out of 10, Exceptional, (16)
"The property was in good condition and owner communicated well in advance. Only issue is the bed is small for two and pillows need to be upgraded."
Cozy 2-Floor Apartment with Garage Access

Leicester Lake Front Home, Come Relax!

10.0 out of 10, Exceptional, (23)
"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 Adjacent 3-Bedroom Family Home Close to Wachusett Mountain!

9.8 out of 10, Exceptional, (85)
"Home was clean and comfortable. My extended family and I stayed two nights for a wedding in the area and a good time was had by all. No complaints with the accommodations and the hosts communicated well."
Lake Adjacent 3-Bedroom Family Home Close to Wachusett Mountain!

Spacious Massachusetts Apartment #2

9.4 out of 10, Exceptional, (15)
"The apartment was clean, stocked with all you need and the location was just off the Main Street so stores and restaurants were walkable. Ample parking behind the unit. Comfortable bedrooms and furniture. "
Spacious Massachusetts Apartment #2

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."
The price is €819
includes taxes & fees
9 Dec - 10 Dec
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. "
Luxury Home, Pool, fireplace

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

8.8 out of 10, Excellent, (3)
"Great place for a short stay to allow us to attend a Bridal shower. Lots of comfortable beds. Thanks."
Beautiful two-story home close to downtown worcester 5beds-4bedroom

Fall Lake Cottage 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...
Fall Lake Cottage near Treehouse Brewery & Amazon Warehouse with King Beds

Cottage on Partridge Pond

10.0 out of 10, Exceptional, (16)
"Lovely home with a small dock in a large pond! Kayaks in the back yard. Beautiful looking out to the pond. Very comfortable home. Hosts are very responsive. We would definitely stay here again. Nice job!"
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

Lake House in Sturbridge w/All the Views!

9.8 out of 10, Exceptional, (6)
"We had a great time in Sturbridge. Can't beat the location of this house - it's absolutely beautiful, and very close to Old Sturbridge Village and a cute coffee shop we frequented during the long weekend. Everything was nice and clean, the hot tub was great, and it was easy to check in. The beds are comfortable and it was nice to not have to worry about the linens upon checkout. The host replied super promptly when we had questions about the location of trash/recycling bins, and when there was...
The price is €1,176
includes taxes & fees
30 Nov - 1 Dec
Lake House in Sturbridge w/All the Views!

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 €311
includes taxes & fees
1 Dec - 2 Dec
Trainmaster's Inn - Caboose

5 bedrooms Home away from Home

10.0 out of 10, Exceptional, (8)
"Everyone loves it "
5 bedrooms Home away from Home

Full family home 200 ft from the lake shore. Dog friendly!

10.0 out of 10, Exceptional, (5)
"Great location for our family visit. Property was very clean. Host very responsive. The beautiful sunrises over the lake were an additional bonus!"
The price is €565
includes taxes & fees
10 Dec - 11 Dec
Full family home 200 ft from the lake shore. Dog friendly!

completely renovated 3 bedroom, 2 bath overlooking idyllic lake whittemore

10.0 out of 10, Exceptional, (180)
"Overall a wonderful stay. This is a duplex and the owner lives next door. Nice neighborhood and beautiful view"
completely renovated 3 bedroom, 2 bath overlooking idyllic lake whittemore

Relaxing Retreat

9.8 out of 10, Exceptional, (24)
"The property was very good. A washer and dryer would have been handy."
Relaxing Retreat
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

Wellsworth Hotel

3.0 star property
9.2 out of 10, Wonderful, (1079)
"I grew up in Southbridge and came back to visit family. I do travel quite a bit and I can honestly say this hotel ranks way up on my list for cleanliness, friendliness of staff, parking, and convenience of location. I very highly recommend this hotel. Thank you for making my visit home such a great experience!"
The price is €104
includes taxes & fees
29 Nov - 30 Nov
Wellsworth Hotel

Great Wolf Lodge Boston / Fitchburg, MA

3.5 star property
8.6 out of 10, Excellent, (811)
"Too bad we have to pay for parking... otherwise very good time with family."
The price is €170
includes taxes & fees
2 Dec - 3 Dec
Great Wolf Lodge Boston / Fitchburg, MA

Comfort Inn Auburn - Worcester

2.5 star property
7.6 out of 10, Good, (745)
"Room are spacious "
The price is €99
includes taxes & fees
11 Dec - 12 Dec
Comfort Inn Auburn - 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?

Beautiful 2 Bedrooms with 2 Beds in Shrewsbury : This holiday home rental outside of Oakham has air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. 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 Great Wolf Lodge Waterpark, 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.