A river surrounded by autumn foliage.

Holiday Homes in Southbridge

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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 Southbridge holiday homes

A wooden bench and a small wooden bridge in a natural setting with greenery and a stream.

1. 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 €192
includes taxes & fees
13 Oct - 14 Oct
Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8
A red building with a colorful mural on the front, a covered porch, and a stone foundation.

2. 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 €172
includes taxes & fees
12 Oct - 13 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.

3. The Tree House at Underhill Hollow

The Tree House at Underhill Hollow
Thompson
9.4 out of 10, Exceptional, (44 reviews)
"Great space, lots of fun."
United States
Douglas C.
The price is €177
includes taxes & fees
14 Oct - 15 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.

4. 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 €172
includes taxes & fees
12 Oct - 13 Oct
SteamPunk Bunk House and Intergalactic Way Station
A hotel with a central building, outdoor seating area, and a covered patio.

5. 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 €476
includes taxes & fees
2 Nov - 3 Nov
Direct waterfront Lake House, stunning views Sleeps 8 on a private PENINSULA!
A grassy outdoor area with a hammock, chairs, and a stone wall.

6. 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 €193
includes taxes & fees
13 Oct - 14 Oct
Little House Inn - Private Home - Secluded - Ware - 2 bedroom, sleeps 6
The Cottage is nestled next to the historic Sagendorph Mansion.

7. 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 €235
includes taxes & fees
12 Oct - 13 Oct
Cottage by the Castle – Downtown Spencer
A spacious deck with wicker furniture, large windows offering a view of a lake and trees, and a wooden ceiling.

8. 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 €778
includes taxes & fees
12 Oct - 13 Oct
Lake House in Sturbridge w/All the Views!
A compact, modern laundry room with a built-in washer and dryer, a small storage cabinet, and a tiled floor.

9. 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 €238
includes taxes & fees
11 Oct - 12 Oct
Angel Sky Challenge
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 €572
includes taxes & fees
1 Nov - 2 Nov
Secluded 2-Acre Lakefront Home! Book Your Getaway!
A window with a view of a grassy field and trees.

11. Spacious, unique barn with beautiful views.

Spacious, unique barn with beautiful views.
Hampton
9.8 out of 10, Exceptional, (7 reviews)
"I was looking for a place that was central to a couple of Renaissance Faires in the area and ended uo choosing this one due to its location and affordability. What an awesome place to stay. We're considering staying here next year when the Faires return."
United States
Kevan W.
The price is €276
includes taxes & fees
12 Oct - 13 Oct
Spacious, unique barn with beautiful views.
A room with a bed, a bookshelf, a TV, a fireplace, and a door leading to another room.

12. 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, (10 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 €328
includes taxes & fees
13 Oct - 14 Oct
Spacious 2,000 Sq Ft New England Retreat - 2BR/2BA Walk to Shops and Restaurants
A living room with a round table, two armchairs, a TV mounted on the wall, and a potted plant.

13. 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 €394
includes taxes & fees
31 Oct - 1 Nov
Beautiful two-story home close to downtown worcester 5beds-4bedroom
A stone wall, a metal gate, and a building with a blue door and a number '74' sign.

14. A Timeless Retreat at Historic Crompton House

A Timeless Retreat at Historic Crompton House
Elm Park
10.0 out of 10, Exceptional, (1 review)
"This is a beautiful property! Great location and amazing hosts! We had everything we needed and were very comfortable. I highly recommend this place!"
United States
Jessica H.
The price is €446
includes taxes & fees
12 Oct - 13 Oct
A Timeless Retreat at Historic Crompton House
A bedroom with a large bed, a desk, a chair, a mirror, and a clock on the wall.

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

Game Room + Bar Lounge, 35 Min to Boston
Worcester
The price is €208
includes taxes & fees
13 Oct - 14 Oct
Game Room + Bar Lounge, 35 Min to Boston
A modern kitchen with a stainless steel refrigerator, double sink, and wooden flooring.

16. 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 €450
includes taxes & fees
14 Oct - 15 Oct
Spacious 4-bedroom with four and half bathrooms
A cozy outdoor seating area with a fire feature, two drinks, and hanging plants.

17. Family-friendly 2- Bedroom Webster Home w/Cozy Balcony

Family-friendly 2- Bedroom Webster Home w/Cozy Balcony
Webster
9.6 out of 10, Exceptional, (5 reviews)
"Owner was easy to communicate with. Cute and cozy unit that meet all of our needs for our trip."
United States
Rachele T.
The price is €559
includes taxes & fees
14 Oct - 15 Oct
Family-friendly 2- Bedroom Webster Home w/Cozy Balcony
A spacious living room with a large sectional sofa, wooden flooring, and a high ceiling with skylights.

18. 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 €1,573
includes taxes & fees
12 Oct - 13 Oct
Sleeps 15 • Pool • Retreat
A staircase with wooden steps and black balusters, a potted plant on a side table, and a framed floral artwork on the wall.

19. 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 €435
includes taxes & fees
18 Oct - 19 Oct
Spacious 5-bedroom home with three full bathrooms in charming Worcester location
A two-story residential building with a front porch, a satellite dish, and a small front yard.

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

Renovated Lakefront 5BR • Near Colleges • Sunsets • Sleeps 12
Worcester
The price is €485
includes taxes & fees
13 Oct - 14 Oct
Renovated Lakefront 5BR • Near Colleges • Sunsets • Sleeps 12
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 Southbridge Hotel Reviews

Comfort Inn Auburn - Worcester

Comfort Inn Auburn - Worcester

10/10 Excellent
"Clean room. Really good breakfast."
Peter 1-night trip
Posted 6 hours ago
Comfort Inn Auburn - Worcester

Find out more about Southbridge

Southbridge Holiday Homes information

Number of reviews
434
Accommodation
104 Holiday Homes
Lowest Price
€172
Highest Price
€1,573