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Wheelwright Holiday Rentals

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Wheelwright holiday rentals

A grassy outdoor area with a hammock, chairs, and a stone wall.

1. Little House Inn - Private Home - Secluded - Ware - 2 bedroom, sleeps 6

Little House Inn - Private Home - Secluded - Ware - 2 bedroom, sleeps 6
Ware
9.8 out of 10, Exceptional, (26 reviews)
"Nice place to stay a lot of family activities on the premises short distance to shopping and attractions"
United States
Andrew
The price is HK$1,253
HK$1,499 total
includes taxes & fees
24 Sept - 25 Sept
Little House Inn - Private Home - Secluded - Ware - 2 bedroom, sleeps 6
A modern living room with a leather sofa, a coffee table, and a dining table. There are two windows providing natural light, a ceiling light fixture, and a trash can.

2. Newly Built Barn Loft in Pioneer Valley

Newly Built Barn Loft in Pioneer Valley
Belchertown
9.6 out of 10, Exceptional, (38 reviews)
"The host was so responsive and made sure everything was perfect! It was the cutest and most comfy set up! With an adorable town beach 5 min down the road! Highly recommend!"
United States
Nora M.
The price is HK$1,235
HK$1,637 total
includes taxes & fees
24 Sept - 25 Sept
Newly Built Barn Loft in Pioneer Valley

3. Cottage by the Castle – Downtown Spencer

Cottage by the Castle – Downtown Spencer
Spencer
10.0 out of 10, Exceptional, (7 reviews)
"The cottage is beautiful, cozy and super comfortable! We loved it! The hosts also were super, communicative and friendly. The place was clean, we had everything we needed, is in a very safe area, and very pretty! Hight recommended! Thank you for hosting us!"
United States
Fabiola
The price is HK$1,616
HK$1,839 total
includes taxes & fees
28 Sept - 29 Sept
Cottage by the Castle – Downtown Spencer
A wooden gazebo with a metal roof, surrounded by a brick patio with outdoor seating.

4. Serene 1-bedroom suite on 75 acre horse property

Serene 1-bedroom suite on 75 acre horse property
Belchertown
10.0 out of 10, Exceptional, (38 reviews)
"Not your average stay! This place is super cool!!"
United States
Wayne B.
The price is HK$1,475
HK$2,462 total
includes taxes & fees
18 Oct - 19 Oct
Serene 1-bedroom suite on 75 acre horse property
A modern kitchen with white cabinets, a stainless steel refrigerator, and a dining area with a table and chairs.

5. Cozy Chic Countryside Haven - Sleeps 4 , Firepit

Cozy Chic Countryside Haven - Sleeps 4 , Firepit
Sturbridge
10.0 out of 10, Exceptional, (3 reviews)
"The place was immaculate, very large room, great kitchen, great bath, plenty of room for a family, quiet and secluded area few minutes away from town, outstanding communication with the property owner..true home away from home...Try it for yourself.."
United States
Giora Y.
The price is HK$1,247
HK$2,558 total
includes taxes & fees
21 Oct - 22 Oct
Cozy Chic Countryside Haven - Sleeps 4 , Firepit
A spacious living room with a wooden ceiling, a grey sofa, a staircase, and a large window.

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

Our pondside cabin - a charming retreat with modern amenities near Wachusett Mtn
Westminster
10.0 out of 10, Exceptional, (37 reviews)
"Very pleasant stay. Would definitely stay here again. "
United States
Shreya
The price is HK$1,765
HK$4,053 total
includes taxes & fees
29 Sept - 30 Sept
Our pondside cabin - a charming retreat with modern amenities near Wachusett Mtn
A spacious deck with wicker furniture, large windows offering a view of a lake and trees, and a wooden ceiling.

7. Lake House in Sturbridge w/All the Views!

Lake House in Sturbridge w/All the Views!
Sturbridge
9.6 out of 10, Exceptional, (23 reviews)
"We really appreciated the kindling and firewood for the outdoor fire pit.The house was clean and nice."
United States
Christian C.
The price is HK$2,392
HK$6,619 total
includes taxes & fees
28 Sept - 29 Sept
Lake House in Sturbridge w/All the Views!
A house with a stone wall and a dock extending into a calm body of water.

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

Lakefront; view of ski mountain, firepit, dock, kayaks, paddle board
Westminster
9.6 out of 10, Exceptional, (42 reviews)
"Very clean and tidy!Tyler was great - even accommodated last minute to add our dogs to the booking!Would definitely stay again!"
United States
Christina C.
The price is HK$1,255
HK$3,519 total
includes taxes & fees
28 Sept - 29 Sept
Lakefront; view of ski mountain, firepit, dock, kayaks, paddle board
A modern kitchen with a stainless steel refrigerator, double sink, and wooden flooring.

9. Spacious 4-bedroom with four and half bathrooms

Spacious 4-bedroom with four and half bathrooms
Worcester
9.8 out of 10, Exceptional, (20 reviews)
"Perfect location"
United States
Harmony F.
The price is HK$2,157
HK$4,031 total
includes taxes & fees
29 Sept - 30 Sept
Spacious 4-bedroom with four and half bathrooms
A modern kitchen with white cabinets, stainless steel appliances, and a central island with bar stools.

10. 4-bedroom house in nice Holden with WiFi, AC

4-bedroom house in nice Holden with WiFi, AC
Holden
10.0 out of 10, Exceptional, (2 reviews)
"Communication with owner was very responsive and timely. House was clean and as description. Any problems were immediately addressed by owner."
United States
larry d.
The price is HK$2,941
HK$4,427 total
includes taxes & fees
24 Sept - 25 Sept
4-bedroom house in nice Holden with WiFi, AC
A wooden bench and a small wooden bridge in a natural setting with greenery and a stream.

11. Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8

Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8
Brimfield
9.2 out of 10, Wonderful, (9 reviews)
"What a beautiful set up for a pet friendly family stay - candles lit upon arrival and a child’s room filled with toys ready to be enjoyed."
United States
Gregory C.
The price is HK$1,242
HK$1,519 total
includes taxes & fees
28 Sept - 29 Sept
Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8
A modern kitchen with white cabinetry, a large island, and pendant lighting.

12. Modern Farmhouse Close to Mt. Wachusett

Modern Farmhouse Close to Mt. Wachusett
Holden
The price is HK$2,224
HK$5,053 total
includes taxes & fees
7 Oct - 8 Oct
Modern Farmhouse Close to Mt. Wachusett

13. Newly Renovated 4BR Worcester Home • Pet-Friendly • Near I-290 & Park 16-2

Newly Renovated 4BR Worcester Home • Pet-Friendly • Near I-290 & Park 16-2
Worcester
10.0 out of 10, Exceptional, (6 reviews)
"Clean, perfect, had everything we needed for a quick stay "
United States
Sierra M.
The price is HK$1,253
HK$3,140 total
includes taxes & fees
27 Sept - 28 Sept
Newly Renovated 4BR Worcester Home • Pet-Friendly • Near I-290 & Park 16-2
A spacious living room with a large sectional sofa, wooden flooring, and a high ceiling with skylights.

14. Sleeps 15 • Pool • Retreat

Sleeps 15 • Pool • Retreat
Brimfield
10.0 out of 10, Exceptional, (39 reviews)
"It was a beautiful property. Well-tended and all the amenities. Loved the view in morning and evening of mountains and sun / moon."
United States
Daniel C.
The price is HK$7,765
HK$13,913 total
includes taxes & fees
1 Oct - 2 Oct
Sleeps 15 • Pool • Retreat
A compact, modern laundry room with a built-in washer and dryer, a small storage cabinet, and a tiled floor.

15. Angel Sky Challenge

Angel Sky Challenge
Worcester
2.0 out of 10, (1 review)
"The add states an entire home, this is a home with small bedrooms and a bathroom. I was under the impression by the description the entire home was ours without others on the property. I’d put that in the description I felt under comfortable with the men on the property. False advertising "
United States
Cameron R.
The price is HK$1,255
HK$2,038 total
includes taxes & fees
24 Sept - 25 Sept
Angel Sky Challenge
A room with two black leather sofas, a glass-top coffee table, white walls, and a ceiling light.

16. Modern Stay 3BR Worcester Apt • FREE Parking near Clark University & I-290 4/1

Modern Stay 3BR Worcester Apt • FREE Parking near Clark University & I-290 4/1
Main South
8.0 out of 10, Very good, (2 reviews)
"The host was very communicative and obviously has tried to make this unit a reasonable place to have people stay. However, the layout of the place was not ideal. They turned a front sitting room into a bedroom, but it doesn't really work well. Further, that room smelled like marijuana our whole stay (1-night). It connected to the stairwell up to the units above, and my guess is that those people just smoke weed all day/night and it's impacting this unit. Further, the outside of the house is...
United States
Jeffrey B.
The price is HK$833
HK$2,408 total
includes taxes & fees
24 Sept - 25 Sept
Modern Stay 3BR Worcester Apt • FREE Parking near Clark University & I-290 4/1
A residential property with a grassy yard, a tree, and a house in the background.

17. Renovated Lakefront 5BR • Near Colleges • Sunsets • Sleeps 12

Renovated Lakefront 5BR • Near Colleges • Sunsets • Sleeps 12
Worcester
The price is HK$3,145
HK$5,862 total
includes taxes & fees
13 Oct - 14 Oct
Renovated Lakefront 5BR • Near Colleges • Sunsets • Sleeps 12

18. Breezy 4BR Worcester Home • Pet-Friendly • Summer Fun near I-290 & Parks 16-3

Breezy 4BR Worcester Home • Pet-Friendly • Summer Fun near I-290 & Parks 16-3
Worcester
10.0 out of 10, Exceptional, (2 reviews)
"Very nice stay. Plenty of space for the 7 of us that stayed, could have easily had 4 more. Recently refinished, so I think Jenny is still getting it all well stocked with kitchen wares. Only down side was window unit AC, which was a bit noisy when trying to watch TV (or for delicate sleepers)"
United States
Andrew O.
The price is HK$1,253
HK$3,167 total
includes taxes & fees
28 Sept - 29 Sept
Breezy 4BR Worcester Home • Pet-Friendly • Summer Fun near I-290 & Parks 16-3

19. FREE Parking & Renovated 4BR Stay 1st-floor Apt Near Clark Uni, Laundry + AC 161

FREE Parking & Renovated 4BR Stay 1st-floor Apt Near Clark Uni, Laundry + AC 161
Worcester
8.0 out of 10, Very good, (5 reviews)
"House was clean, modern, and family friendly. It met the needs for our family gathering of 10. We had space for fun/games and gathering for meals. The area was quiet. Easy to fet to downtown Worcester , highways, and restaurants."
United States
Abby M.
The price is HK$1,327
HK$3,260 total
includes taxes & fees
28 Sept - 29 Sept
FREE Parking & Renovated 4BR Stay 1st-floor Apt Near Clark Uni, Laundry + AC 161
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 Wheelwright Hotel Reviews

Comfort Inn & Suites Sturbridge - Brimfield

Comfort Inn & Suites Sturbridge - Brimfield

10/10 Excellent
"Super clean and updated rooms. Friendly staff. Great breakfast, but get there early. Nice area to walk my dogs. Would definitely stay here again."
michele 1-night trip
Posted 18 hours ago
Comfort Inn & Suites Sturbridge - Brimfield

Find out more about Wheelwright

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

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Look no further and take a look at our great range of rental properties in Wheelwright!

Frequently asked questions

Can I find a holiday rental in Wheelwright?

Yes, there are holiday rentals close to the most popular sights in Wheelwright, 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 Wheelwright has to offer?

Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8: This holiday home rental outside of Wheelwright is located in a rural location, and has a garden, a selection of games and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

What can I see and do in Wheelwright?

While exploring the area, visit family-friendly sights like Wilton s Children Store, or get outside and enjoy nature at Rock House Reservation. In the wider area, you’ll find Barre Historical Society and Hardwick Vineyard and Winery.

What are holiday rentals like in Wheelwright?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Wheelwright. Holiday rentals offer extras such as laundry facilities and kitchens so you'll have everything you need. If you're concerned about a clean environment, a holiday rental can offer a sense of security away from shared hotel lifts and busy lobbies while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a hotel, which makes a holiday rental an attractive option for small groups.