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Wheelwright Vacation Rentals

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Check prices for these dates

In two weeks
Jul 3 - Jul 5
In two months
Aug 14 - Aug 16
In three months
Sep 11 - Sep 13
In four months
Oct 9 - Oct 11

Our top choices for Wheelwright vacation rentals

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.
The price is ￥25,638
￥41,447 total
includes taxes & fees
Jun 19 - Jun 20
Angel Sky Challenge
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.
The price is ￥24,036
￥55,129 total
includes taxes & fees
Jul 1 - Jul 2
Trainmaster's Inn - Caboose
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, (29 reviews)
"Very pleasant stay. Would definitely stay here again. "
United States
Shreya
The price is ￥36,072
￥82,308 total
includes taxes & fees
Jun 30 - Jul 1
Our pondside cabin - a charming retreat with modern amenities near Wachusett Mtn
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, (14 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 ￥28,858
￥34,400 total
includes taxes & fees
Jun 17 - Jun 18
Little House Inn - Private Home - Secluded - Ware - 2 bedroom, sleeps 6
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, (37 reviews)
"Cutest home! My family loved it! "
United States
Shanna D.
The price is ￥56,084
￥108,986 total
includes taxes & fees
Jul 6 - Jul 7
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, (28 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.
The price is ￥21,152
￥39,634 total
includes taxes & fees
Jun 18 - Jun 19
Serene 1-bedroom suite on 75 acre horse property
Apartment (3 Bedrooms) | Interior

1 Mi to Downtown & Palladium: Worcester Getaway!

1 Mi to Downtown & Palladium: Worcester Getaway!
3.0 star property
Worcester
10.0 out of 10, Exceptional, (1 review)
"The place was amazing, just needed a few updates and repairs, but nothing that made our stay bad or inconvenient. "
United States
Michelle
The price is ￥25,812
￥78,360 total
includes taxes & fees
Jun 20 - Jun 21
1 Mi to Downtown & Palladium: Worcester Getaway!
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, (28 reviews)
"The place was really nice! Very clean and well decorated. We had a great short stay and would definitely book it again in the future."
United States
Emily O.
The price is ￥25,238
￥33,790 total
includes taxes & fees
Jun 24 - Jun 25
Newly Built Barn Loft in Pioneer Valley
Interior

Cozy Chic Countryside Haven - Sleeps 4 , Firepit

Cozy Chic Countryside Haven - Sleeps 4 , Firepit
Sturbridge
10.0 out of 10, Exceptional, (1 review)
"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 ￥32,529
￥61,214 total
includes taxes & fees
Jun 18 - Jun 19
Cozy Chic Countryside Haven - Sleeps 4 , Firepit
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
9.2 out of 10, Wonderful, (5 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
The price is ￥32,529
￥40,988 total
includes taxes & fees
Jun 22 - Jun 23
Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8
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, (1 review)
"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.
The price is ￥35,912
￥70,275 total
includes taxes & fees
Jul 8 - Jul 9
Beautiful Worcester Downtown King Bd/Office World Cup Boston
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.
The price is ￥44,066
￥81,977 total
includes taxes & fees
Jun 22 - Jun 23
Spacious 4-bedroom with four and half bathrooms
Private kitchen

4-bedroom house in nice Holden with WiFi, AC

4-bedroom house in nice Holden with WiFi, AC
Holden
The price is ￥60,090
￥89,768 total
includes taxes & fees
Jul 7 - Jul 8
4-bedroom house in nice Holden with WiFi, AC
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.
The price is ￥70,044
￥123,100 total
includes taxes & fees
Jun 30 - Jul 1
Newly Renovated 4BR Worcester Home • Pet-Friendly • Near I-290 & Park 16-2
TV, fireplace

Sleeps 15 • Pool • World Cup 2026 • Retreat

Sleeps 15 • Pool • World Cup 2026 • Retreat
Brimfield
10.0 out of 10, Exceptional, (34 reviews)
"We visited in December, so the pool was closed, but looked inviting even in the snow. The home was so warm and cozy and spacious. We loved our stay."
United States
Gina O.
The price is ￥158,638
￥284,234 total
includes taxes & fees
Jun 19 - Jun 20
Sleeps 15 • Pool • World Cup 2026 • Retreat
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)
The price is ￥30,646
￥66,985 total
includes taxes & fees
Jun 24 - Jun 25
Cozy 3BR Worcester Apt • Pet-Friendly near Clark University & I-290 4/1
Fridge, microwave, stovetop, coffee/tea maker

Renovated 4BR Worcester Home • Pet-Friendly near I-290 & Parks 16-1

Renovated 4BR Worcester Home • Pet-Friendly near I-290 & Parks 16-1
Worcester
9.4 out of 10, Exceptional, (3 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 ￥28,875
￥68,259 total
includes taxes & fees
Jun 17 - Jun 18
Renovated 4BR Worcester Home • Pet-Friendly near I-290 & Parks 16-1
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

Publick House Historic Inn and Country Motor Lodge

Publick House Historic Inn and Country Motor Lodge

10/10 Excellent
"We loved the look of the property and the rooms. There was a lot of character in the rooms, decorated with furniture from the colonial time period, yet up to date in modern conveniences. We stayed in the king suite in the Chamberline House. It was like our own apartment. Restaurants on site were good and the breakfast provided by the bake shop was a nice treat. It was so close to Sturbridge Village and that was our original reason for staying there, but after being at the Publick House, we would go back even if we weren’t going to Sturbridge Village."
Cecelia 2-night trip
Posted less than an hour ago
Publick House Historic Inn and Country Motor Lodge

Find out more about Wheelwright

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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.