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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

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, (23 reviews)
"Nice place to stay a lot of family activities on the premises short distance to shopping and attractions"
United States
Andrew
$171 nightly
The price is $180
Aug 24 - Aug 25
Total with taxes and fees
Little House Inn - Private Home - Secluded - Ware - 2 bedroom, sleeps 6

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.
$236 nightly
The price is $238
Aug 24 - Aug 25
Total with taxes and fees
Cottage by the Castle – Downtown Spencer
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, (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.
$204 nightly
The price is $215
Aug 24 - Aug 25
Total with taxes and fees
Newly Built Barn Loft in Pioneer Valley
A wooden gazebo with a metal roof, surrounded by a brick patio with outdoor seating.

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
$221 nightly
The price is $234
Aug 31 - Sep 1
Total with taxes and fees
Serene 1-bedroom suite on 75 acre horse property
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.
$286 nightly
The price is $319
Sep 14 - Sep 15
Total with taxes and fees
Cozy Chic Countryside Haven - Sleeps 4 , Firepit
A compact, modern laundry room with a built-in washer and dryer, a small storage cabinet, and a tiled floor.

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.
$229 nightly
The price is $262
Aug 24 - Aug 25
Total with taxes and fees
Angel Sky Challenge
A spacious living room with a wooden ceiling, a grey sofa, a staircase, and a large window.

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
$474 nightly
The price is $520
Aug 31 - Sep 1
Total with taxes and fees
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.

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.
$171 nightly
The price is $191
Aug 24 - Aug 25
Total with taxes and fees
Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8
A house with a stone wall and a dock extending into a calm body of water.

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.
$454 nightly
The price is $498
Sep 7 - Sep 8
Total with taxes and fees
Lakefront; view of ski mountain, firepit, dock, kayaks, paddle board
A room with two black leather sofas, a glass-top coffee table, white walls, and a ceiling light.

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.
$283 nightly
The price is $324
Aug 24 - Aug 25
Total with taxes and fees
Modern Stay 3BR Worcester Apt • FREE Parking near Clark University & I-290 4/1

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.
$330 nightly
The price is $377
Aug 24 - Aug 25
Total with taxes and fees
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.

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.
$452 nightly
The price is $517
Aug 24 - Aug 25
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.

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.
$537 nightly
The price is $568
Aug 24 - Aug 25
Total with taxes and fees
4-bedroom house in nice Holden with WiFi, AC

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.
$452 nightly
The price is $517
Sep 1 - Sep 2
Total with taxes and fees
Breezy 4BR Worcester Home • Pet-Friendly • Summer Fun near I-290 & Parks 16-3
A spacious living room with a large sectional sofa, wooden flooring, and a high ceiling with skylights.

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.
$1,459 nightly
The price is $1,629
Aug 31 - Sep 1
Total with taxes and fees
Sleeps 15 • Pool • Retreat

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.
$353 nightly
The price is $404
Aug 27 - Aug 28
Total with taxes and fees
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

Super 8 by Wyndham Sturbridge

Super 8 by Wyndham Sturbridge

8/10 Good
"Great hotel with lots of updates. Not at all what you'd expect from a typical Super 8. Just make sure you get there early for breakfast. It's nice that they offer a breakfast, don't get me wrong, but there isn't much on offer, and if you are there after 8:30, they do not replenish anything. We got there at 8:40 and all that was left besides the waffle maker was 3 slices of bread for toasting and one muffin. My suggestion to the hotel, either extend your breakfast hours or replenish your offerings until your posted end time. That is my only complaint. Everything else is fantastic."
Thomas 1-night trip
Posted 11 hours ago
Super 8 by Wyndham Sturbridge

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 $180 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?

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.