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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

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
9.6 out of 10, Exceptional, (28 reviews)
"This was a super cozy ,cute place to stay . Host had muffins , juice and milk for us. The property was quiet and very peaceful."
United States
theresa H.
The price is £141
includes taxes & fees
12 Nov - 13 Nov
Little House Inn - Private Home - Secluded - Ware - 2 bedroom, sleeps 6
The Cottage is nestled next to the historic Sagendorph Mansion.

2. Cottage by the Castle – Downtown Spencer

Cottage by the Castle – Downtown Spencer
Spencer
10.0 out of 10, Exceptional, (9 reviews)
"Nice, clean and well maintained. Would stay here again."
United States
Sarah S.
The price is £188
includes taxes & fees
18 Nov - 19 Nov
Cottage by the Castle – Downtown Spencer
A wooden gazebo with a metal roof, surrounded by a brick patio with outdoor seating.

3. 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, (40 reviews)
"We had a great, restorative stay in Liberty Woods. It is a lovely oasis with kind humans, friendly animals and beautiful horses in a beautiful setting."
United States
Anna O.
The price is £195
includes taxes & fees
30 Nov - 1 Dec
Serene 1-bedroom suite on 75 acre horse property
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.

4. Newly Built Barn Loft in Pioneer Valley

Newly Built Barn Loft in Pioneer Valley
Belchertown
9.6 out of 10, Exceptional, (39 reviews)
"Great place for a couple to stay. Hostess was fantastic. We had everything we needed. Would definitely recommend and would stay again!"
United States
Doreen R.
The price is £172
includes taxes & fees
16 Nov - 17 Nov
Newly Built Barn Loft in Pioneer Valley
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, (4 reviews)
"Gorgeously decorated and ultra-clean. Was the perfect rental for my sisters wedding at Salem Cross Inn"
United States
Trish N.
The price is £274
includes taxes & fees
17 Nov - 18 Nov
Cozy Chic Countryside Haven - Sleeps 4 , Firepit
A compact, modern laundry room with a built-in washer and dryer, a small storage cabinet, and a tiled floor.

6. 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 £184
includes taxes & fees
8 Dec - 9 Dec
Angel Sky Challenge
A wooden cabin bedroom with a bed, a nightstand, a lamp, and a bunk bed.

7. The Christmas Cottage, 4BR New England Escape

The Christmas Cottage, 4BR New England Escape
Rutland
The price is £550
includes taxes & fees
18 Nov - 19 Nov
The Christmas Cottage, 4BR New England Escape
A wooden fence with a rustic appearance, surrounded by lush greenery and purple flowers.

8. Two Bedroom Guesthouse near many attractions pet friendly with private deck

Two Bedroom Guesthouse near many attractions pet friendly with private deck
Gardner
10.0 out of 10, Exceptional, (3 reviews)
"Cute little guesthouse. Super clean and lovely decorated."
United States
Kristin R.
The price is £243
includes taxes & fees
8 Dec - 9 Dec
Two Bedroom Guesthouse near many attractions pet friendly with private deck
A spacious living room with a wooden ceiling, a grey sofa, a staircase, and a large window.

9. 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, (40 reviews)
"Very pleasant stay. Would definitely stay here again. "
United States
Shreya
The price is £362
includes taxes & fees
18 Nov - 19 Nov
Our pondside cabin - a charming retreat with modern amenities near Wachusett Mtn
Two Adirondack chairs on a wooden deck with a view of a lake and trees.

10. Worcester Lakefront Cottage Apt w/ Shared Dock!

Worcester Lakefront Cottage Apt w/ Shared Dock!
Worcester
9.4 out of 10, Exceptional, (19 reviews)
"The host was very accommodating and responsive. Great property in a great location, would stay again!"
United States
Michaela H.
The price is £328
includes taxes & fees
22 Nov - 23 Nov
Worcester Lakefront Cottage Apt w/ Shared Dock!
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, (12 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 £162
includes taxes & fees
14 Nov - 15 Nov
Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8
Living area

12. 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 £257
includes taxes & fees
11 Nov - 12 Nov
Newly Renovated 4BR Worcester Home • Pet-Friendly • Near I-290 & Park 16-2
A modern kitchen with white cabinets, stainless steel appliances, and a central island with bar stools.

13. 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, (3 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 £483
includes taxes & fees
22 Nov - 23 Nov
4-bedroom house in nice Holden with WiFi, AC
A room with two black leather sofas, a glass-top coffee table, white walls, and a ceiling light.

14. 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
8.8 out of 10, Excellent, (3 reviews)
"Rented the property to attend a series of events at Clark University. Literally walking distance to the school so it was quite convenient. Apartment was clean, beds were comfortable. Being able to park three cars in the driveway was a huge plus as street parking near the apartment was extremely challenging. Being a Clark alum, was quite familiar with the neighborhood so I knew what to expect. Felt completely safe in the apartment as every door to the hallways had sufficient locks. We did blow a...
United States
Elyse D.
The price is £227
includes taxes & fees
1 Dec - 2 Dec
Modern Stay 3BR Worcester Apt • FREE Parking near Clark University & I-290 4/1
Two Adirondack chairs on a wooden deck with a view of a lake and trees.

15. Worcester Lakefront Cottage Apt w/ Shared Dock!

Worcester Lakefront Cottage Apt w/ Shared Dock!
3.0 star property
Worcester
The price is £337
includes taxes & fees
22 Nov - 23 Nov
Worcester Lakefront Cottage Apt w/ Shared Dock!
A lakeside cabin with a deck, a dock, and a small docked boat.

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

Direct waterfront Lake House, stunning views Sleeps 8 on a private PENINSULA!
Sturbridge
9.8 out of 10, Exceptional, (98 reviews)
"very clean, wonderful location"
United States
Anonymous traveller
The price is £360
includes taxes & fees
11 Nov - 12 Nov
Direct waterfront Lake House, stunning views Sleeps 8 on a private PENINSULA!
A spacious living room with a large sectional sofa, wooden flooring, and a high ceiling with skylights.

17. Sleeps 15 • Pool • Retreat

Sleeps 15 • Pool • Retreat
Brimfield
10.0 out of 10, Exceptional, (40 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 £1,296
includes taxes & fees
8 Dec - 9 Dec
Sleeps 15 • Pool • Retreat
A balcony with a table and chairs, overlooking a street with houses and parked cars.

18. Cozy 3BR Apt | Steps to Clark University

Cozy 3BR Apt | Steps to Clark University
Main South
The price is £300
includes taxes & fees
1 Dec - 2 Dec
Cozy 3BR Apt | Steps to Clark University
A spacious deck with wicker furniture, large windows offering a view of a lake and trees, and a wooden ceiling.

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

Lake House in Sturbridge w/All the Views!
Sturbridge
9.6 out of 10, Exceptional, (25 reviews)
"Pictures don't do this house justice! Great communication from start to finish, very clean house & property, coolest house we've ever stayed at. Hope to stay again!"
United States
Mike T.
Lake House in Sturbridge w/All the Views!
A modern kitchen with a stainless steel refrigerator, double sink, and wooden flooring.

20. Spacious 4-bedroom with four and half bathrooms

Spacious 4-bedroom with four and half bathrooms
Worcester
9.8 out of 10, Exceptional, (23 reviews)
"Great, clean location to stay."
United States
Mike O.
The price is £365
includes taxes & fees
18 Nov - 19 Nov
Spacious 4-bedroom with four and half bathrooms
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

A white colonial-style house with a symmetrical facade, a central entrance, and a well-maintained garden with colorful flowers.
Publick House Historic Inn and Country Motor Lodge

Publick House Historic Inn and Country Motor Lodge

Publick House Historic Inn and Country Motor Lodge
Sturbridge

10/10 Excellent

Due to issues at Boston Logan Airport, we unexpectedly arrived at Publick House Historic Inn without a rental car. This beautiful hotel is spread over a large area and the room we were intended to occupy was some driving distance from the main reception. With no car, we were unable to take the room set aside for us, but were immediately upgraded to a room just steps away and could not have been more grateful to the friendly and welcoming staff.
United Kingdom
Adrian
Reviewed August 31, 2025
Publick House Historic Inn and Country Motor Lodge

Find out more about Wheelwright

Everything you need to know about Wheelwright holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Wheelwright holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Wheelwright holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Wheelwright holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Wheelwright. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Wheelwright holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Wheelwright holiday rentals we have selected for you start as low as £141 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Wheelwright rentals

At Expedia, we put the best Wheelwright holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Wheelwright rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Wheelwright holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Wheelwright. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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.