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Wheelwright Vacation Rentals

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Check prices for these dates

In two weeks
Sep 4 - Sep 6
In two months
Oct 16 - Oct 18
In three months
Nov 13 - Nov 15
In four months
Dec 11 - Dec 13

Our top choices for Wheelwright vacation rentals

Property grounds

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, (22 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 CA $231
CA $275 total
includes taxes & fees
Aug 21 - Aug 22
Little House Inn - Private Home - Secluded - Ware - 2 bedroom, sleeps 6
Exterior

2. Cottage by the Castle – Downtown Spencer

Cottage by the Castle – Downtown Spencer
Spencer
10.0 out of 10, Exceptional, (3 reviews)
"Nice, clean and well maintained. Would stay here again."
United States
Sarah S.
The price is CA $286
CA $326 total
includes taxes & fees
Aug 23 - Aug 24
Cottage by the Castle – Downtown Spencer
Smart TV, books, stereo

3. Newly Built Barn Loft in Pioneer Valley

Newly Built Barn Loft in Pioneer Valley
Belchertown
9.6 out of 10, Exceptional, (34 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 CA $219
CA $293 total
includes taxes & fees
Aug 23 - Aug 24
Newly Built Barn Loft in Pioneer Valley
Outdoor dining

4. 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, (34 reviews)
"This was an amazing nightly rate for the region, and a lovely place to visit. I'm so glad we found it and was available! Brent and family take great care of the place, and it was so magical waking up and seeing horses just a few feet from the window. We had fun playing games under the gazebo while horses munched on hay. There's lots of good hiking in the area too. The suite had everything we needed like extra blankets, kitchen wares, games, and a great shower too. Highly recommended!"
United States
Elizabeth
The price is CA $164
CA $319 total
includes taxes & fees
Aug 31 - Sep 1
Serene 1-bedroom suite on 75 acre horse property
Interior

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 $208
CA $439 total
includes taxes & fees
Sep 14 - Sep 15
Cozy Chic Countryside Haven - Sleeps 4 , Firepit
Interior

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 CA $222
CA $360 total
includes taxes & fees
Aug 31 - Sep 1
Angel Sky Challenge
Smart TV

7. 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 $313
CA $720 total
includes taxes & fees
Aug 31 - Sep 1
Our pondside cabin - a charming retreat with modern amenities near Wachusett Mtn
Property grounds

8. 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, (8 reviews)
"Welcoming, cute."
United States
Trinity M.
The price is CA $235
CA $295 total
includes taxes & fees
Aug 23 - Aug 24
Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8
Exterior

9. 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, (41 reviews)
"Beautiful location and perfect for a fishing getaway! House was clean and cozy!"
United States
Julianne R.
The price is CA $277
CA $688 total
includes taxes & fees
Sep 16 - Sep 17
Lakefront; view of ski mountain, firepit, dock, kayaks, paddle board
Interior

10. 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.
The price is CA $181
CA $471 total
includes taxes & fees
Aug 20 - Aug 21
Modern Stay 3BR Worcester Apt • FREE Parking near Clark University & I-290 4/1
Smart TV

11. 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 $209
CA $545 total
includes taxes & fees
Aug 20 - Aug 21
Newly Renovated 4BR Worcester Home • Pet-Friendly • Near I-290 & Park 16-2
Coffee/tea maker, fridge, microwave, oven

12. Spacious 4-bedroom with four and half bathrooms

Spacious 4-bedroom with four and half bathrooms
Worcester
10.0 out of 10, Exceptional, (17 reviews)
"Perfect location"
United States
Harmony F.
The price is CA $382
CA $711 total
includes taxes & fees
Aug 31 - Sep 1
Spacious 4-bedroom with four and half bathrooms
Private kitchen

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, (1 review)
"The house was located in a quiet, nice, pleasant, neighborhood. The rooms were spacious and comfortable. The house was very clean and the beds were comfortable. The house was located near all kinds of stores, pharmacy’s, and good restaurants. I’d I had to make a negative comment it would be that all the bedrooms were on the second floor which was tough for two of our party. The property owner was quick to respond to questions we had. Overall, a very pleasant stay."
United States
Samantha R.
The price is CA $521
CA $786 total
includes taxes & fees
Aug 23 - Aug 24
4-bedroom house in nice Holden with WiFi, AC
Coffee/tea maker, fridge, microwave, oven

14. 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.
The price is CA $201
CA $534 total
includes taxes & fees
Aug 20 - Aug 21
Breezy 4BR Worcester Home • Pet-Friendly • Summer Fun near I-290 & Parks 16-3
TV, fireplace

15. Sleeps 15 • Pool • Retreat

Sleeps 15 • Pool • Retreat
Brimfield
10.0 out of 10, Exceptional, (38 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 $1,220
CA $2,255 total
includes taxes & fees
Aug 31 - Sep 1
Sleeps 15 • Pool • Retreat
Coffee/tea maker, fridge, microwave, stovetop

16. FREE Parking & Renovated 4BR Stay 1st-floor Apt Near Clark Uni, Laundry + AC 161

FREE Parking & Renovated 4BR Stay 1st-floor Apt Near Clark Uni, Laundry + AC 161
Worcester
9.6 out of 10, Exceptional, (4 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 CA $203
CA $536 total
includes taxes & fees
Aug 20 - Aug 21
FREE Parking & Renovated 4BR Stay 1st-floor Apt Near Clark Uni, Laundry + AC 161
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 & Suites Sturbridge by IHG

Holiday Inn Express & Suites Sturbridge by IHG

10/10 Excellent
"I was pleasantly surprised by this very reasonably priced hotel about a stone's throw from Sturbridge Village, right off the Mass Pike. I don't know if it's recently remodeled, but everything looks new. Super clean and spacious room, lots of channels on the TV, lots of plugs for devices, good shower, microwave and fridge that actually is cold. I didn't do breakfast, and the pool is unfortunately. undergoing maintenance, but this is a great place to stay for travelers. (A Panera is across the parking lot.) I go out to Western Mass often, and this is a good middle-of-the-trip location. I'll be back!"
Alicia 1-night trip
Posted 4 hours ago
Holiday Inn Express & Suites Sturbridge 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, 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 $275 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?

Direct waterfront Lake House, stunning views Sleeps 8 on a private PENINSULA!: Visitors like this Wheelwright vacation home rental. It is located on a lake and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a private yard 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 Rock House Reservation. In the larger area, you’ll find Hardwick Vineyard and Winery and Saint Joseph's Abbey.

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.