A river surrounded by autumn foliage.

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Check prices for these dates

In two weeks
14 Aug - 16 Aug
In two months
25 Sep - 27 Sep
In three months
23 Oct - 25 Oct
In four months
20 Nov - 22 Nov

Our top choices for Southbridge vacation homes

Interior

1. The Tree House at Underhill Hollow

The Tree House at Underhill Hollow
Thompson
9.4 out of 10, Exceptional, (39 reviews)
"Nice place to stay has good air conditioning "
United States
Zachary P.
The price is AED 463
AED 711 total
includes taxes & fees
2 Aug - 3 Aug
The Tree House at Underhill Hollow
Exterior

2. Wizard's Roost at Underhill Hollow

Wizard's Roost at Underhill Hollow
North Grosvenordale
9.6 out of 10, Exceptional, (24 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 AED 463
AED 690 total
includes taxes & fees
13 Aug - 14 Aug
Wizard's Roost at Underhill Hollow
Property grounds

3. SteamPunk Bunk House and Intergalactic Way Station

SteamPunk Bunk House and Intergalactic Way Station
Thompson
10.0 out of 10, Exceptional, (16 reviews)
"Enjoyed our stay. Loved being out in the countryside "
United States
Pauline S.
The price is AED 463
AED 690 total
includes taxes & fees
2 Aug - 3 Aug
SteamPunk Bunk House and Intergalactic Way Station
Property grounds

4. 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, (7 reviews)
"Welcoming, cute."
United States
Trinity M.
The price is AED 720
AED 890 total
includes taxes & fees
1 Sep - 2 Sep
Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8
Exterior

5. 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 AED 841
AED 957 total
includes taxes & fees
5 Aug - 6 Aug
Cottage by the Castle – Downtown Spencer
Dining

6. Beautiful Worcester Downtown King Bd/Office World Cup Boston

Beautiful Worcester Downtown King Bd/Office World Cup Boston
Worcester
10.0 out of 10, Exceptional, (2 reviews)
The price is AED 551
AED 1,282 total
includes taxes & fees
17 Aug - 18 Aug
Beautiful Worcester Downtown King Bd/Office World Cup Boston
Interior

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

Lake House in Sturbridge w/All the Views!
Sturbridge
9.6 out of 10, Exceptional, (22 reviews)
"Thank you for a wonderful stay! Our family enjoyed the gorgeous views and the well-equipped home. There were toys, books, and games for the kids, and the beds were very comfortable. We’d definitely stay again!"
United States
Caitlin D.
The price is AED 1,561
AED 3,637 total
includes taxes & fees
13 Aug - 14 Aug
Lake House in Sturbridge w/All the Views!
Interior

8. Spacious, unique barn with beautiful views.

Spacious, unique barn with beautiful views.
Hampton
9.6 out of 10, Exceptional, (5 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 AED 612
AED 971 total
includes taxes & fees
4 Aug - 5 Aug
Spacious, unique barn with beautiful views.
Outdoor dining

9. Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD

Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD
Ashford
9.6 out of 10, Exceptional, (22 reviews)
"The location of the home was perfect. The lake was beautiful and was a great place to walk. "
United States
Lynn D.
The price is AED 827
AED 1,528 total
includes taxes & fees
18 Aug - 19 Aug
Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD
Property grounds

10. 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, (21 reviews)
"Everything was as we hoped. A wonderful country place in the woods!"
United States
Anthony L.
The price is AED 760
AED 908 total
includes taxes & fees
12 Aug - 13 Aug
Little House Inn - Private Home - Secluded - Ware - 2 bedroom, sleeps 6
Property grounds

11. Lakefront Cottage 2 Mi to Palladium in Worcester!

Lakefront Cottage 2 Mi to Palladium in Worcester!
Worcester
9.8 out of 10, Exceptional, (17 reviews)
"Great hosts and very clean house. We were very comfortable and it has a great view!"
United States
Jeff S.
Lakefront Cottage 2 Mi to Palladium in Worcester!
Interior

12. 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 AED 588
AED 950 total
includes taxes & fees
2 Aug - 3 Aug
Angel Sky Challenge
Dining

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

Secluded 2-Acre Lakefront Home! Book Your Getaway!
Woodstock
9.8 out of 10, Exceptional, (87 reviews)
"The hosts were welcoming and the house was very clean and a great place to stay!"
United States
Emma S.
The price is AED 1,745
AED 2,839 total
includes taxes & fees
2 Aug - 3 Aug
Secluded 2-Acre Lakefront Home! Book Your Getaway!
Property grounds

14. 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
10.0 out of 10, Exceptional, (94 reviews)
"Amazing place to gather and relax. "
United States
Evan M.
The price is AED 2,297
AED 3,526 total
includes taxes & fees
9 Aug - 10 Aug
Direct waterfront Lake House, stunning views Sleeps 8 on a private PENINSULA!
2 bedrooms, iron/ironing board, WiFi, bed sheets

15. 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
10.0 out of 10, Exceptional, (6 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 AED 655
AED 1,442 total
includes taxes & fees
4 Aug - 5 Aug
Spacious 2,000 Sq Ft New England Retreat - 2BR/2BA Walk to Shops and Restaurants
Coffee/tea maker, fridge, microwave, oven

16. Spacious 4-bedroom with four and half bathrooms

Spacious 4-bedroom with four and half bathrooms
Worcester
10.0 out of 10, Exceptional, (15 reviews)
"Perfect location"
United States
Harmony F.
The price is AED 1,010
AED 1,888 total
includes taxes & fees
8 Aug - 9 Aug
Spacious 4-bedroom with four and half bathrooms
Coffee/tea maker, fridge, microwave, oven

17. Mohegan Sun Getaway Large Group Retreat

Mohegan Sun Getaway Large Group Retreat
Killingly
7.4 out of 10, Good, (3 reviews)
"Great setup. Perfect crash pad for a weekend of the Natchaug Epic bike race in Thompson… slept 8 no problem. Host was helpful and beds were clean, kitchens were just what we needed"
United States
shawn c b.
The price is AED 790
AED 2,690 total
includes taxes & fees
5 Aug - 6 Aug
Mohegan Sun Getaway Large Group Retreat
Terrace/patio

18. Stunning Lakefront Escape! Book Your Dream Getaway!

Stunning Lakefront Escape! Book Your Dream Getaway!
Woodstock
10.0 out of 10, Exceptional, (27 reviews)
"Great experience. Thank you "
United States
edmund d.
The price is AED 1,653
AED 2,723 total
includes taxes & fees
2 Aug - 3 Aug
Stunning Lakefront Escape! Book Your Dream Getaway!
TV

19. 6 Beds Home w/Game Room Perfect for Groups

6 Beds Home w/Game Room Perfect for Groups
Killingly
6 Beds Home w/Game Room Perfect for Groups
Interior

20. Cozy 3-bedroom house in serene Worcester with fitness room and office

Cozy 3-bedroom house in serene Worcester with fitness room and office
Worcester
10.0 out of 10, Exceptional, (2 reviews)
"The only thing missing was a BBQ"
United States
Charmen B.
The price is AED 1,818
AED 2,379 total
includes taxes & fees
31 Aug - 1 Sep
Cozy 3-bedroom house in serene Worcester with fitness room and office
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

Wellsworth Hotel

Wellsworth Hotel

10/10 Excellent
"Beautiful building, clean room. Staff were so friendly and helpful, and the pool was awesome!"
Kristy 1-night trip
Posted 12 hours ago
Wellsworth Hotel

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