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Wheelwright Vacation Rentals

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Wheelwright vacation rentals

A wooden gazebo with a metal roof, surrounded by a brick patio with outdoor seating.

1. 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.
$237 nightly
The price is $251
Oct 18 - Oct 19
Total with taxes and fees
Serene 1-bedroom suite on 75 acre horse property
A grassy outdoor area with a hammock, chairs, and a stone wall.

2. 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)
"Nice place to stay a lot of family activities on the premises short distance to shopping and attractions"
United States
Andrew
$202 nightly
The price is $214
Oct 13 - Oct 14
Total with taxes and fees
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.

3. 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.
$201 nightly
The price is $212
Oct 12 - Oct 13
Total with taxes and fees
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, (8 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
$261 nightly
The price is $263
Oct 12 - Oct 13
Total with taxes and fees
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.
$282 nightly
The price is $315
Oct 18 - Oct 19
Total with taxes and fees
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
$468 nightly
The price is $513
Oct 22 - Oct 23
Total with taxes and fees
Our pondside cabin - a charming retreat with modern amenities near Wachusett Mtn
A compact, modern laundry room with a built-in washer and dryer, a small storage cabinet, and a tiled floor.

7. 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.
$229 nightly
The price is $262
Oct 10 - Oct 11
Total with taxes and fees
Angel Sky Challenge
A stone wall, a metal gate, and a building with a blue door and a number '74' sign.

8. A Timeless Retreat at Historic Crompton House

A Timeless Retreat at Historic Crompton House
Elm Park
10.0 out of 10, Exceptional, (1 review)
"This is a beautiful property! Great location and amazing hosts! We had everything we needed and were very comfortable. I highly recommend this place!"
United States
Jessica H.
$437 nightly
The price is $500
Oct 12 - Oct 13
Total with taxes and fees
A Timeless Retreat at Historic Crompton House
A lakeside cabin with a dock, a boat, and a second-story deck.

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

Lakefront; view of ski mountain, firepit, dock, kayaks, laundry, outdoor shower
Westminster
10.0 out of 10, Exceptional, (42 reviews)
"We had a great stay with our family."
United States
Sherri P.
$413 nightly
The price is $453
Oct 12 - Oct 13
Total with taxes and fees
Lakefront; view of ski mountain, firepit, dock, kayaks, laundry, outdoor shower
A house with a stone wall and a dock extending into a calm body of water.

10. 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.
$409 nightly
The price is $449
Oct 15 - Oct 16
Total with taxes and fees
Lakefront; view of ski mountain, firepit, dock, kayaks, paddle board
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, (10 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.
$188 nightly
The price is $210
Oct 13 - Oct 14
Total with taxes and fees
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.

12. 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.
Modern Stay 3BR Worcester Apt • FREE Parking near Clark University & I-290 4/1
Living area

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.
Newly Renovated 4BR Worcester Home • Pet-Friendly • Near I-290 & Park 16-2
A two-story residential building with a front porch, a satellite dish, and a small front yard.

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

Renovated Lakefront 5BR • Near Colleges • Sunsets • Sleeps 12
Worcester
$481 nightly
The price is $551
Oct 13 - Oct 14
Total with taxes and fees
Renovated Lakefront 5BR • Near Colleges • Sunsets • Sleeps 12
A modern kitchen with a stainless steel refrigerator, double sink, and wooden flooring.

15. 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)
"10/10 great place to stay"
United States
Tyler B.
$446 nightly
The price is $510
Oct 14 - Oct 15
Total with taxes and fees
Spacious 4-bedroom with four and half bathrooms
A modern kitchen with white cabinets, stainless steel appliances, and a central island with bar stools.

16. 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.
$534 nightly
The price is $564
Nov 1 - Nov 2
Total with taxes and fees
4-bedroom house in nice Holden with WiFi, AC
A spacious deck with wicker furniture, large windows offering a view of a lake and trees, and a wooden ceiling.

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

Lake House in Sturbridge w/All the Views!
Sturbridge
9.6 out of 10, Exceptional, (24 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.
$795 nightly
The price is $869
Oct 12 - Oct 13
Total with taxes and fees
Lake House in Sturbridge w/All the Views!
A staircase with wooden steps and black balusters, a potted plant on a side table, and a framed floral artwork on the wall.

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
$431 nightly
The price is $493
Oct 18 - Oct 19
Total with taxes and fees
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.
$700 nightly
The price is $782
Nov 1 - Nov 2
Total with taxes and fees
3br Lakefront Oasis in Shutesbury with central air and 180-deg views!
Private kitchen

20. 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.
Breezy 4BR Worcester Home • Pet-Friendly • Summer Fun 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

Comfort Inn & Suites Sturbridge - Brimfield

Comfort Inn & Suites Sturbridge - Brimfield

10/10 Excellent
"Nice room. Good staff. Clean"
jeff 1-night trip
Posted 10 hours ago
Comfort Inn & Suites Sturbridge - Brimfield

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, condos, resorts, cabins, villas, motels. 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 low season months. For more hustle and bustle, you may prefer to visit Wheelwright in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $210 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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.