Wheelwright Vacation Rentals

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Check prices for these dates

Next weekend
Nov 13 - Nov 15
In two weeks
Nov 20 - Nov 22
In one month
Dec 4 - Dec 6
In two months
Jan 1 - Jan 3

Our top choices for Wheelwright vacation homes

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
9.6 out of 10, Exceptional, (28 reviews)
"This was a super cozy ,cute place to stay . Host had muffins , juice and milk for us. The property was quiet and very peaceful."
United States
theresa H.
The price is CA $216
CA $246 total
includes taxes & fees
Nov 9 - Nov 10
Little House Inn - Private Home - Secluded - Ware - 2 bedroom, sleeps 6
The Cottage is nestled next to the historic Sagendorph Mansion.

2. Cottage by the Castle – Downtown Spencer

Cottage by the Castle – Downtown Spencer
Spencer
10.0 out of 10, Exceptional, (9 reviews)
"Nice, clean and well maintained. Would stay here again."
United States
Sarah S.
The price is CA $291
CA $318 total
includes taxes & fees
Nov 9 - Nov 10
Cottage by the Castle – Downtown Spencer
A wooden cabin bedroom with a bed, a nightstand, a lamp, and a bunk bed.

3. The Christmas Cottage, 4BR New England Escape

The Christmas Cottage, 4BR New England Escape
Rutland
The price is CA $494
CA $1,054 total
includes taxes & fees
Nov 9 - Nov 10
The Christmas Cottage, 4BR New England Escape
A compact, modern laundry room with a built-in washer and dryer, a small storage cabinet, and a tiled floor.

4. 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 $226
CA $335 total
includes taxes & fees
Nov 9 - Nov 10
Angel Sky Challenge
Two Adirondack chairs on a wooden deck with a view of a lake and trees.

5. Worcester Lakefront Cottage Apt w/ Shared Dock!

Worcester Lakefront Cottage Apt w/ Shared Dock!
Worcester
9.4 out of 10, Exceptional, (19 reviews)
"The host was very accommodating and responsive. Great property in a great location, would stay again!"
United States
Michaela H.
The price is CA $249
CA $623 total
includes taxes & fees
Nov 22 - Nov 23
Worcester Lakefront Cottage Apt w/ Shared Dock!
A wooden bench and a small wooden bridge in a natural setting with greenery and a stream.

6. 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, (12 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.
The price is CA $254
CA $308 total
includes taxes & fees
Nov 15 - Nov 16
Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8
A modern kitchen with white cabinets, stainless steel appliances, and a central island with bar stools.

7. 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, (3 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.
The price is CA $671
CA $924 total
includes taxes & fees
Nov 22 - Nov 23
4-bedroom house in nice Holden with WiFi, AC
A lakeside cabin with a deck, a dock, and a small docked boat.

8. Direct waterfront Lake House, stunning views Sleeps 8 on a private PENINSULA!

Direct waterfront Lake House, stunning views Sleeps 8 on a private PENINSULA!
Sturbridge
9.8 out of 10, Exceptional, (98 reviews)
"very clean, wonderful location"
United States
Anonymous traveller
The price is CA $318
CA $641 total
includes taxes & fees
Nov 9 - Nov 10
Direct waterfront Lake House, stunning views Sleeps 8 on a private PENINSULA!
A modern kitchen with a stainless steel refrigerator, double sink, and wooden flooring.

9. 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)
"Great, clean location to stay."
United States
Mike O.
The price is CA $389
CA $661 total
includes taxes & fees
Nov 9 - Nov 10
Spacious 4-bedroom with four and half bathrooms
A spacious living room with a large sectional sofa, wooden flooring, and a high ceiling with skylights.

10. Sleeps 15 • Pool • Retreat

Sleeps 15 • Pool • Retreat
Brimfield
10.0 out of 10, Exceptional, (40 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 $1,399
CA $2,506 total
includes taxes & fees
Nov 10 - Nov 11
Sleeps 15 • Pool • Retreat
A spacious deck with wicker furniture, large windows offering a view of a lake and trees, and a wooden ceiling.

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

Lake House in Sturbridge w/All the Views!
Sturbridge
9.6 out of 10, Exceptional, (25 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.
The price is CA $374
CA $1,030 total
includes taxes & fees
Nov 9 - Nov 10
Lake House in Sturbridge w/All the Views!
A lakeside residential area with houses along the water's edge, a dock, and a boat.

12. 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.
The price is CA $635
CA $1,088 total
includes taxes & fees
Nov 10 - Nov 11
3br Lakefront Oasis in Shutesbury with central air and 180-deg views!
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 reviews in Wheelwright

A hotel entrance with a covered walkway, columns, and a brick facade.
Holiday Inn Express & Suites Sturbridge by IHG

Holiday Inn Express & Suites Sturbridge by IHG

Holiday Inn Express & Suites Sturbridge by IHG
Sturbridge

10/10 Excellent

Great stay
Canada
Tyler
Reviewed May 3, 2026
Holiday Inn Express & Suites Sturbridge by IHG

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