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Wheelwright Vacation Rentals

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Check prices for these dates

In two weeks
Jul 24 - Jul 26
In two months
Sep 4 - Sep 6
In three months
Oct 2 - Oct 4
In four months
Oct 30 - Nov 1

Our top choices for Wheelwright vacation rentals

Interior

Trainmaster's Inn - Caboose

Trainmaster's Inn - Caboose
Palmer
9.4 out of 10, Exceptional, (10 reviews)
"A great stay in a vintage RR caboose. Thanks to everyone at Trainmasters Inn!"
United States
Edward L.
$315 nightly
The price is $352
Jul 8 - Jul 9
Total with taxes and fees
Trainmaster's Inn - Caboose
Smart TV, books, stereo

Newly Built Barn Loft in Pioneer Valley

Newly Built Barn Loft in Pioneer Valley
Belchertown
9.6 out of 10, Exceptional, (31 reviews)
"Kitchen was clean and well stocked with water, and some small snacks. "
United States
Cheyenne K.
$201 nightly
The price is $212
Jul 8 - Jul 9
Total with taxes and fees
Newly Built Barn Loft in Pioneer Valley
Exterior

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, (38 reviews)
"Cutest home! My family loved it! "
United States
Shanna D.
$406 nightly
The price is $445
Jul 12 - Jul 13
Total with taxes and fees
Lakefront; view of ski mountain, firepit, dock, kayaks, paddle board
Outdoor dining

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, (29 reviews)
"We had a lovely weekend, it was quiet, private and watching the horses in the pasture was wonderful. We would definitely stay again. "
United States
Kim G.
$219 nightly
The price is $232
Jul 13 - Jul 14
Total with taxes and fees
Serene 1-bedroom suite on 75 acre horse property
Interior

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
Jul 8 - Jul 9
Total with taxes and fees
Angel Sky Challenge
Interior

Spacious Massachusetts Apartment #2

Spacious Massachusetts Apartment #2
West Brookfield
9.0 out of 10, Wonderful, (30 reviews)
"Really a cute place to stay, very clean and comfortable "
United States
Michelle J.
$303 nightly
The price is $338
Jul 9 - Jul 10
Total with taxes and fees
Spacious Massachusetts Apartment #2
Property grounds

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
9.4 out of 10, Exceptional, (6 reviews)
"This is a nice place for solo travelers or a small family with kids. The kid’s bedroom has tons of games and is themed nicely. The backyard is huge but unfenced and the property is off of a busy road. Th house itself was clean and the host offered a variety of things such as slippers for the whole family, house shoes, and bath things for everyone. The house does not have a tv but the wifi works well. "
United States
Chantay-Rose
$192 nightly
The price is $215
Jul 8 - Jul 9
Total with taxes and fees
Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8
Exterior

Cottage by the Castle – Downtown Spencer

Cottage by the Castle – Downtown Spencer
Spencer
10.0 out of 10, Exceptional, (1 review)
"Wonderful stay in the cottage. Great location, and prompt and friendly communication from the owner. Beautifully kept vintage home - such a gem!"
United States
K C.
$189 nightly
The price is $190
Jul 8 - Jul 9
Total with taxes and fees
Cottage by the Castle – Downtown Spencer
3 bedrooms, iron/ironing board, free WiFi, bed sheets

Apartment in town center #1

Apartment in town center #1
West Brookfield
8.8 out of 10, Excellent, (28 reviews)
"Stayed here to visit Treehouse brewing with some friends and it was perfect. "
United States
Chris G.
$296 nightly
The price is $330
Jul 8 - Jul 9
Total with taxes and fees
Apartment in town center #1
Interior

Cozy 3BR Worcester Apt • Pet-Friendly near Clark University & I-290 4/1

Cozy 3BR Worcester Apt • Pet-Friendly near Clark University & I-290 4/1
Main South
10.0 out of 10, Exceptional, (1 review)
$316 nightly
The price is $362
Jul 12 - Jul 13
Total with taxes and fees
Cozy 3BR Worcester Apt • Pet-Friendly near Clark University & I-290 4/1
Smart TV

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, (4 reviews)
"Clean, perfect, had everything we needed for a quick stay "
United States
Sierra M.
$421 nightly
The price is $481
Jul 13 - Jul 14
Total with taxes and fees
Newly Renovated 4BR Worcester Home • Pet-Friendly • Near I-290 & Park 16-2
Smart TV

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, (33 reviews)
"Very pleasant stay. Would definitely stay here again. "
United States
Shreya
$512 nightly
The price is $562
Aug 5 - Aug 6
Total with taxes and fees
Our pondside cabin - a charming retreat with modern amenities near Wachusett Mtn
Interior

Cozy Chic Countryside Haven - Sleeps 4 , Firepit

Cozy Chic Countryside Haven - Sleeps 4 , Firepit
Sturbridge
10.0 out of 10, Exceptional, (2 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.
$323 nightly
The price is $361
Jul 29 - Jul 30
Total with taxes and fees
Cozy Chic Countryside Haven - Sleeps 4 , Firepit
House (2 Bedrooms) | Front of property

Lakefront Cottage 2 Mi to Palladium in Worcester!

Lakefront Cottage 2 Mi to Palladium in Worcester!
3.0 star property
Worcester
$395 nightly
The price is $452
Jul 19 - Jul 20
Total with taxes and fees
Lakefront Cottage 2 Mi to Palladium in Worcester!
Property grounds

Lakefront Cottage 2 Mi to Palladium in Worcester!

Lakefront Cottage 2 Mi to Palladium in Worcester!
Worcester
9.8 out of 10, Exceptional, (17 reviews)
"Great host! Easy to contact via text. Home was clean and perfect for my family!"
United States
Michael B.
$393 nightly
The price is $446
Jul 19 - Jul 20
Total with taxes and fees
Lakefront Cottage 2 Mi to Palladium in Worcester!
Dining

Beautiful Worcester Downtown King Bd/Office World Cup Boston

Beautiful Worcester Downtown King Bd/Office World Cup Boston
Worcester
10.0 out of 10, Exceptional, (2 reviews)
"I had an amazing stay here and would absolutely recommend this place to anyone visiting Boston or Worcester, Massachusetts. The house was truly 100% excellent. Everything was incredibly clean, spacious, and well organized. I loved the kitchen, my room, and the bathroom, everything was spotless and very comfortable. Honestly, the entire home was sparkling clean and very welcoming.I also slept extremely well during my stay. The bed, pillows, and bedding were so comfortable, which made the...
United States
Masard T.
$341 nightly
The price is $390
Jul 26 - Jul 27
Total with taxes and fees
Beautiful Worcester Downtown King Bd/Office World Cup Boston
Property grounds

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, (19 reviews)
"Nice place to stay a lot of family activities on the premises short distance to shopping and attractions"
United States
Andrew
$207 nightly
The price is $219
Aug 3 - Aug 4
Total with taxes and fees
Little House Inn - Private Home - Secluded - Ware - 2 bedroom, sleeps 6
Fridge, microwave, oven, stovetop

Spacious 4-bedroom with four and half bathrooms

Spacious 4-bedroom with four and half bathrooms
Worcester
10.0 out of 10, Exceptional, (12 reviews)
"10/10 great place to stay"
United States
Tyler B.
$446 nightly
The price is $510
Jul 13 - Jul 14
Total with taxes and fees
Spacious 4-bedroom with four and half bathrooms
Terrace/patio

Spacious Getaway by TreeHouse Brewery & Amazon WareHouse

Spacious Getaway by TreeHouse Brewery & Amazon WareHouse
Charlton
8.6 out of 10, Excellent, (25 reviews)
"It’s very clean with lots of room for the price. The neighborhood is quiet and peaceful. The pool is well-maintained. The owner is very responsive and helpful. Highly recommend!"
United States
Jan L.
$781 nightly
The price is $826
Jul 28 - Jul 29
Total with taxes and fees
Spacious Getaway by TreeHouse Brewery & Amazon WareHouse
Private kitchen

4-bedroom house in nice Holden with WiFi, AC

4-bedroom house in nice Holden with WiFi, AC
Holden
$423 nightly
The price is $447
Jul 9 - Jul 10
Total with taxes and fees
4-bedroom house in nice Holden with WiFi, AC
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

Holiday Inn Express Hotel & Suites Auburn by IHG

Holiday Inn Express Hotel & Suites Auburn by IHG

8/10 Good
"We called ahead to ensure late check-in would be possible; the gentleman at the front desk desk was very polite, efficient and professional as we arrived at nearly midnight. however, the lady at the front desk during check-out was cold and unfriendly, curtly instructing us to drop the key cards in the box and gruffly said, "you're good to go". so, there is some unevenness with staff professionalism, but we did not have to interact with them much at all."
Madhu 4-night trip
Posted 1 hour ago
Holiday Inn Express Hotel & Suites Auburn by IHG

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 $190 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 - Private Home - Secluded - Ware - 2 bedroom, sleeps 6: Visitors like this Wheelwright vacation home rental. It is located in a rural location and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. Kick off your shoes and enjoy yourself with a garden and a selection of games.

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 Barre Common District. In the larger area, you’ll find Hardwick Vineyard and Winery and Rock House Reservation.

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.