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Wheelwright Vacation Rentals

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Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for Wheelwright vacation 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, (27 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 CA $237
CA $282 total
includes taxes & fees
Oct 27 - Oct 28
Little House Inn - Private Home - Secluded - Ware - 2 bedroom, sleeps 6
A wooden gazebo with a metal roof, surrounded by a brick patio with outdoor seating.

2. 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 CA $180
CA $344 total
includes taxes & fees
Oct 28 - Oct 29
Serene 1-bedroom suite on 75 acre horse property
A modern living room with a black sofa, a coffee table, and a wicker basket. A kitchen with white cabinets and a black countertop is visible in the background.

3. Newly Built Barn Loft in Pioneer Valley

Newly Built Barn Loft in Pioneer Valley
Belchertown
9.6 out of 10, Exceptional, (39 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 CA $221
CA $295 total
includes taxes & fees
Oct 27 - Oct 28
Newly Built Barn Loft in Pioneer Valley
The Cottage is nestled next to the historic Sagendorph Mansion.

4. 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 CA $320
CA $369 total
includes taxes & fees
Oct 28 - Oct 29
Cottage by the Castle – Downtown Spencer
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 CA $210
CA $441 total
includes taxes & fees
Nov 10 - Nov 11
Cozy Chic Countryside Haven - Sleeps 4 , Firepit
A wooden cabin bedroom with a bed, a nightstand, a lamp, and a bunk bed.

6. The Christmas Cottage, 4BR New England Escape

The Christmas Cottage, 4BR New England Escape
Rutland
The price is CA $490
CA $1,100 total
includes taxes & fees
Nov 24 - Nov 25
The Christmas Cottage, 4BR New England Escape
A house with a stone wall and a dock extending into a calm body of water.

7. 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)
"Lovely, quiet retreat. Great host, easy check in and out."
United States
Jeff W.
The price is CA $168
CA $555 total
includes taxes & fees
Oct 25 - Oct 26
Lakefront; view of ski mountain, firepit, dock, kayaks, paddle board
A compact, modern laundry room with a built-in washer and dryer, a small storage cabinet, and a tiled floor.

8. 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 CA $224
CA $367 total
includes taxes & fees
Oct 25 - Oct 26
Angel Sky Challenge
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, (37 reviews)
"Very pleasant stay. Would definitely stay here again. "
United States
Shreya
The price is CA $315
CA $719 total
includes taxes & fees
Nov 3 - Nov 4
Our pondside cabin - a charming retreat with modern amenities near Wachusett Mtn
A wooden bench and a small wooden bridge in a natural setting with greenery and a stream.

10. 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 CA $233
CA $293 total
includes taxes & fees
Oct 28 - Oct 29
Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8
A room with two black leather sofas, a glass-top coffee table, white walls, and a ceiling light.

11. 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 CA $187
CA $482 total
includes taxes & fees
Nov 1 - Nov 2
Modern Stay 3BR Worcester Apt • FREE Parking near Clark University & I-290 4/1
A modern kitchen with white cabinets, stainless steel appliances, and a central island with bar stools.

12. 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 CA $465
CA $715 total
includes taxes & fees
Oct 26 - Oct 27
4-bedroom house in nice Holden with WiFi, AC
A hotel with a central building, outdoor seating area, and a covered patio.

13. 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 CA $347
CA $702 total
includes taxes & fees
Nov 2 - Nov 3
Direct waterfront Lake House, stunning views Sleeps 8 on a private PENINSULA!
A spacious deck with wicker furniture, large windows offering a view of a lake and trees, and a wooden ceiling.

14. 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.
The price is CA $469
CA $1,251 total
includes taxes & fees
Oct 25 - Oct 26
Lake House in Sturbridge w/All the Views!
Living area

15. 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 CA $257
CA $604 total
includes taxes & fees
Oct 25 - Oct 26
Newly Renovated 4BR Worcester Home • Pet-Friendly • Near I-290 & Park 16-2
A modern kitchen with a stainless steel refrigerator, double sink, and wooden flooring.

16. 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 CA $385
CA $721 total
includes taxes & fees
Oct 29 - Oct 30
Spacious 4-bedroom with four and half bathrooms
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 CA $1,386
CA $2,478 total
includes taxes & fees
Oct 29 - Oct 30
Sleeps 15 • Pool • Retreat
A hotel room with a bed, bedside table, lamp, potted plant, and a desk with a chair.

18. Spacious 5-bedroom home with three full bathrooms in charming Worcester location

Spacious 5-bedroom home with three full bathrooms in charming Worcester location
Worcester
The price is CA $504
CA $694 total
includes taxes & fees
Oct 27 - Oct 28
Spacious 5-bedroom home with three full bathrooms in charming Worcester location
A lakeside residential area with houses along the water's edge, a dock, and a boat.

19. 3br Lakefront Oasis in Shutesbury with central air and 180-deg views!

3br Lakefront Oasis in Shutesbury with central air and 180-deg views!
Shutesbury
10.0 out of 10, Exceptional, (2 reviews)
"We had a great time at the house. Perfect for family and young kids. Very clean. View of lake and bald eagles! were amazing. Host was very responsive and provided a lot of extra info on location places to eat, events, etc. Would definitely stay again."
United States
Tara I.
The price is CA $511
CA $984 total
includes taxes & fees
Nov 1 - Nov 2
3br Lakefront Oasis in Shutesbury with central air and 180-deg views!
Private kitchen

20. Breezy 4BR Worcester Home • Pet-Friendly Near I-290 & Parks 16-3

Breezy 4BR Worcester Home • Pet-Friendly 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 CA $268
CA $618 total
includes taxes & fees
Oct 25 - Oct 26
Breezy 4BR Worcester Home • Pet-Friendly Near I-290 & Parks 16-3
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

enVision Hotel Worcester Downtown

enVision Hotel Worcester Downtown

10/10 Excellent
"Stayed here for a concert at the palladium. Was a quick and safe walk to the venue. Property was very clean, helpful friendly staff and parking was easy and convenient. Will definitely be staying here again the next time I’m in the area!"
Zachary 1-night trip
Posted 6 hours ago
enVision Hotel Worcester Downtown

Find out more about Wheelwright

Everything you need to know about Wheelwright vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Wheelwright vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Wheelwright vacation 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Wheelwright vacation rentals we have selected for you start as low as CA $282 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 vacation 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 vacation.

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 vacation rental in Wheelwright?

Yes, there are vacation rentals near popular points of interest in Wheelwright, or you can select a secluded option if you're looking for relaxation.

What's the top vacation rental that Wheelwright has to offer?

Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8: Visitors like this Wheelwright vacation home rental. It is located in a rural location and has a garden, a selection of games, and a barbecue grill 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 larger area, you’ll find Barre Historical Society and Hardwick Vineyard and Winery.

What are vacation rentals like in Wheelwright?

Vacation rentals are privately owned accommodations you can stay in for a short or long stay in Wheelwright. Vacation rentals feature amenities such as kitchens and laundry facilities so you'll have everything you want. If you're concerned about cleanliness, vacation rentals can offer a sense of security away from shared hotel elevators and bustling concierge desks while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular choice for a small group gathering.