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Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for Sturbridge holiday homes

A spacious deck with wicker furniture, large windows offering a view of a lake and trees, and a wooden ceiling.

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

Lake House in Sturbridge w/All the Views!
Sturbridge
9.6 out of 10, Exceptional, (24 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 HK$1,962
HK$6,099 total
includes taxes & fees
7 Oct - 8 Oct
Lake House in Sturbridge w/All the Views!
A wooden bench and a small wooden bridge in a natural setting with greenery and a stream.

2. 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, (10 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 HK$1,099
HK$1,403 total
includes taxes & fees
6 Oct - 7 Oct
Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8
A grassy outdoor area with a hammock, chairs, and a stone wall.

3. 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, (27 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 HK$1,428
HK$1,700 total
includes taxes & fees
3 Nov - 4 Nov
Little House Inn - Private Home - Secluded - Ware - 2 bedroom, sleeps 6
The Cottage is nestled next to the historic Sagendorph Mansion.

4. Cottage by the Castle – Downtown Spencer

Cottage by the Castle – Downtown Spencer
Spencer
10.0 out of 10, Exceptional, (8 reviews)
"The cottage is beautiful, cozy and super comfortable! We loved it! The hosts also were super, communicative and friendly. The place was clean, we had everything we needed, is in a very safe area, and very pretty! Hight recommended! Thank you for hosting us!"
United States
Fabiola
The price is HK$1,796
HK$2,045 total
includes taxes & fees
12 Oct - 13 Oct
Cottage by the Castle – Downtown Spencer
A spacious living room with a large sectional sofa, wooden flooring, and a high ceiling with skylights.

5. Sleeps 15 • Pool • Retreat

Sleeps 15 • Pool • Retreat
Brimfield
10.0 out of 10, Exceptional, (39 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 HK$7,769
HK$13,894 total
includes taxes & fees
7 Oct - 8 Oct
Sleeps 15 • Pool • Retreat
A red building with a colorful mural on the front, a covered porch, and a stone foundation.

6. Wizard's Roost at Underhill Hollow

Wizard's Roost at Underhill Hollow
North Grosvenordale
9.6 out of 10, Exceptional, (26 reviews)
"I stayed here for the 2026 Natchaug Epic gravel bike ride, and it was an ideal location, close to the start line. A charming property with a friendly host. "
United States
Mateo A.
The price is HK$989
HK$1,475 total
includes taxes & fees
6 Oct - 7 Oct
Wizard's Roost at Underhill Hollow
A room with a sloped ceiling, wooden beams, a purple door, and a star decoration on the wall.

7. The Tree House at Underhill Hollow

The Tree House at Underhill Hollow
Thompson
9.4 out of 10, Exceptional, (42 reviews)
"Great space, lots of fun."
United States
Douglas C.
The price is HK$989
HK$1,520 total
includes taxes & fees
7 Oct - 8 Oct
The Tree House at Underhill Hollow
A rustic building with a brick exterior and a red roof, situated next to a pond with tall reeds and a tree with autumn-colored leaves.

8. SteamPunk Bunk House and Intergalactic Way Station

SteamPunk Bunk House and Intergalactic Way Station
Thompson
10.0 out of 10, Exceptional, (18 reviews)
"Enjoyed our stay. Loved being out in the countryside "
United States
Pauline S.
The price is HK$989
HK$1,475 total
includes taxes & fees
6 Oct - 7 Oct
SteamPunk Bunk House and Intergalactic Way Station
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)
"10/10 great place to stay"
United States
Tyler B.
The price is HK$2,158
HK$4,051 total
includes taxes & fees
6 Oct - 7 Oct
Spacious 4-bedroom with four and half bathrooms
A dining area with a high ceiling, skylights, and a view of the outdoors.

10. Secluded 2-Acre Lakefront Home! Book Your Getaway!

Secluded 2-Acre Lakefront Home! Book Your Getaway!
Woodstock
9.8 out of 10, Exceptional, (93 reviews)
"The hosts were welcoming and the house was very clean and a great place to stay!"
United States
Emma S.
The price is HK$2,943
HK$5,069 total
includes taxes & fees
1 Nov - 2 Nov
Secluded 2-Acre Lakefront Home! Book Your Getaway!
A compact, modern laundry room with a built-in washer and dryer, a small storage cabinet, and a tiled floor.

11. 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 HK$1,256
HK$2,057 total
includes taxes & fees
6 Oct - 7 Oct
Angel Sky Challenge
A bedroom with a large bed, a desk, a chair, a mirror, and a clock on the wall.

12. Game Room + Bar Lounge, 35 Min to Boston

Game Room + Bar Lounge, 35 Min to Boston
Worcester
The price is HK$1,313
HK$1,682 total
includes taxes & fees
6 Oct - 7 Oct
Game Room + Bar Lounge, 35 Min to Boston
A living room with two brown leather sofas, a glass coffee table, a white rug, a ceiling fan, and a door with curtains.

13. Cozy 3-bedroom Duplex1 with WiFi, AC in peaceful Springfield

Cozy 3-bedroom Duplex1 with WiFi, AC in peaceful Springfield
Boston Road
8.6 out of 10, Excellent, (21 reviews)
"Location was perfect for us; 10 minutes from family. Host was responsive; we had a lovely stay in Springfield."
United States
Beth P.
The price is HK$1,413
HK$3,063 total
includes taxes & fees
6 Oct - 7 Oct
Cozy 3-bedroom Duplex1 with WiFi, AC in peaceful Springfield
A room with a treadmill, exercise equipment, a desk, and a potted plant.

14. Spacious 5-bedroom home with three full bathrooms in charming Worcester location

Spacious 5-bedroom home with three full bathrooms in charming Worcester location
Worcester
The price is HK$2,825
HK$3,898 total
includes taxes & fees
6 Oct - 7 Oct
Spacious 5-bedroom home with three full bathrooms in charming Worcester location
A living room with two sofas, a coffee table, and a potted plant.

15. Cozy 3-bedroom Duplex2 in beautiful Springfield with WiFi, central AC

Cozy 3-bedroom Duplex2 in beautiful Springfield with WiFi, central AC
Boston Road
9.2 out of 10, Wonderful, (13 reviews)
"Great stay"
United States
Angelina O.
The price is HK$1,413
HK$3,063 total
includes taxes & fees
6 Oct - 7 Oct
Cozy 3-bedroom Duplex2 in beautiful Springfield with WiFi, central AC
A cozy outdoor seating area with a fire feature, two drinks, and hanging plants.

16. Family-friendly 5-Bedroom Webster Home w/ Cozy Balcony - Perfect for Families!

Family-friendly 5-Bedroom Webster Home w/ Cozy Balcony - Perfect for Families!
Webster
10.0 out of 10, Exceptional, (3 reviews)
"We loved the space, it accommodated our larger group and had all the amenities we needed. We only stayed 1 night but would have loved to stay longer! The porch area was very nice to sit out on at night."
United States
Kyle C.
Family-friendly 5-Bedroom Webster Home w/ Cozy Balcony - Perfect for Families!
A room with a bed, a bookshelf, a TV, a fireplace, and a door leading to another room.

17. Spacious 2,000 Sq Ft New England Retreat - 2BR/2BA Walk to Shops and Restaurants

Spacious 2,000 Sq Ft New England Retreat - 2BR/2BA Walk to Shops and Restaurants
Somers
9.6 out of 10, Exceptional, (9 reviews)
"This is a real gem of a find! I loved our stay here. GPS does take you to the back of the building but it’s located next to a large parking lot. Plenty of parking which was great for us because we have an extended cab f350 ford that does not fit into most parking spaces. The other great thing about this house is multiple showers and bathrooms. This is so rare in a CT house. I must’ve searched for hours. The host Pam was super friendly and was so quick to respond. The house was super stocked with...
United States
Jenny
The price is HK$1,236
HK$2,863 total
includes taxes & fees
7 Oct - 8 Oct
Spacious 2,000 Sq Ft New England Retreat - 2BR/2BA Walk to Shops and Restaurants
A two-story residential building with a front porch, a satellite dish, and a small front yard.

18. Renovated Lakefront 5BR • Near Colleges • Sunsets • Sleeps 12

Renovated Lakefront 5BR • Near Colleges • Sunsets • Sleeps 12
Worcester
The price is HK$2,166
HK$4,625 total
includes taxes & fees
13 Oct - 14 Oct
Renovated Lakefront 5BR • Near Colleges • Sunsets • Sleeps 12
A living room with a round table, two armchairs, a TV mounted on the wall, and a potted plant.

19. Beautiful two-story home close to downtown worcester 5beds-4bedroom

Beautiful two-story home close to downtown worcester 5beds-4bedroom
Worcester
9.0 out of 10, Wonderful, (20 reviews)
"Great house-clean, great location."
United States
Kathleen R.
The price is HK$1,750
HK$3,485 total
includes taxes & fees
31 Oct - 1 Nov
Beautiful two-story home close to downtown worcester 5beds-4bedroom
A living room with a sofa, a clock, a floor lamp, and a rug.

20. Beautiful 2 Bedrooms with 2 Beds in Shrewsbury

Beautiful 2 Bedrooms with 2 Beds in Shrewsbury
Shrewsbury
9.4 out of 10, Exceptional, (55 reviews)
"Amazing host and fabulous spacious property. "
United States
Kelly L.
The price is HK$1,264
HK$2,333 total
includes taxes & fees
13 Oct - 14 Oct
Beautiful 2 Bedrooms with 2 Beds in Shrewsbury
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 Sturbridge Hotel Reviews

Wellsworth Hotel

Wellsworth Hotel

10/10 Excellent
"The staff was very nice, the room was well maintained. Our daughter loved the pool. Really, no complaints!"
John 2-night trip
Posted 9 hours ago
Wellsworth Hotel

Find out more about Sturbridge

Sturbridge Vacation Homes information

Number of reviews
412
Accommodation
119 Vacation Homes
Lowest Price
HK$1,403
Highest Price
HK$13,894

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