Autumn forest landscape over Cedar Brook on Old Sturbridge Village Road in Massachusetts

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Check prices for these dates

In two weeks
26 Jun - 28 Jun
In two months
7 Aug - 9 Aug
In three months
4 Sep - 6 Sep
In four months
2 Oct - 4 Oct

Our top choices for Southbridge vacation homes

Interior

The Tree House at Underhill Hollow

The Tree House at Underhill Hollow
Thompson
9.4 out of 10, Exceptional, (37 reviews)
"Such a fun getaway!"
United States
Patrice D.
The price is AED 463
AED 715 total
includes taxes & fees
18 Jun - 19 Jun
The Tree House at Underhill Hollow
Interior

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 942 total
includes taxes & fees
15 Jun - 16 Jun
Angel Sky Challenge
Exterior

Wizard's Roost at Underhill Hollow

Wizard's Roost at Underhill Hollow
North Grosvenordale
9.6 out of 10, Exceptional, (22 reviews)
"Full of whimsy, loved all of the details of the construction and decor. Great place to stay"
United States
Meghann H.
The price is AED 463
AED 690 total
includes taxes & fees
21 Jun - 22 Jun
Wizard's Roost at Underhill Hollow
Interior

Spacious, unique barn with beautiful views.

Spacious, unique barn with beautiful views.
Hampton
10.0 out of 10, Exceptional, (3 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
17 Jun - 18 Jun
Spacious, unique barn with beautiful views.
Property grounds

SteamPunk Bunk House and Intergalactic Way Station

SteamPunk Bunk House and Intergalactic Way Station
Thompson
10.0 out of 10, Exceptional, (14 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
18 Jun - 19 Jun
SteamPunk Bunk House and Intergalactic Way Station
Property grounds

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, (13 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 AED 661
AED 788 total
includes taxes & fees
17 Jun - 18 Jun
Little House Inn - Private Home - Secluded - Ware - 2 bedroom, sleeps 6
Outdoor dining

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

Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD
Ashford
9.6 out of 10, Exceptional, (21 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 949
AED 1,682 total
includes taxes & fees
21 Jun - 22 Jun
Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD
Fridge, microwave, oven, coffee/tea maker

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.
Mohegan Sun Getaway Large Group Retreat
Property grounds

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, (5 reviews)
"This is a nice place for solo travelers or a small family with kids. The kid’s bedroom has tons of games and is themed nicely. The backyard is huge but unfenced and the property is off of a busy road. Th house itself was clean and the host offered a variety of things such as slippers for the whole family, house shoes, and bath things for everyone. The house does not have a tv but the wifi works well. "
United States
Chantay-Rose
The price is AED 746
AED 940 total
includes taxes & fees
22 Jun - 23 Jun
Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8
Dining

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, (1 review)
"I had an amazing stay here and would absolutely recommend this place to anyone visiting Boston or Worcester, Massachusetts. The house was truly 100% excellent. Everything was incredibly clean, spacious, and well organized. I loved the kitchen, my room, and the bathroom, everything was spotless and very comfortable. Honestly, the entire home was sparkling clean and very welcoming.I also slept extremely well during my stay. The bed, pillows, and bedding were so comfortable, which made the...
United States
Masard T.
The price is AED 823
AED 1,623 total
includes taxes & fees
8 Jul - 9 Jul
Beautiful Worcester Downtown King Bd/Office World Cup Boston
2 bedrooms, iron/ironing board, WiFi, bed sheets

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, (1 review)
"This place was perfect for our needs! It was about 5 minutes from the event we came for which was great. Seeing it was a new listing without any reviews I was slightly skeptical but traveling with a 5 year old, a hotel is always a struggle. This place was everything it was advertised and then some. Absolutely spacious, nicely decorated and plenty plenty plenty of little extras like snacks, toiletries, and a very nice and accommodating host! The furniture was all comfortable and good quality,...
United States
Colleen S.
The price is AED 641
AED 1,303 total
includes taxes & fees
21 Jun - 22 Jun
Spacious 2,000 Sq Ft New England Retreat - 2BR/2BA Walk to Shops and Restaurants
Interior

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, (1 review)
"The only thing missing was a BBQ"
United States
Charmen B.
The price is AED 1,286
AED 1,682 total
includes taxes & fees
21 Jun - 22 Jun
Cozy 3-bedroom house in serene Worcester with fitness room and office
Fridge, microwave, oven, stovetop

Spacious 4-bedroom with four and half bathrooms

Spacious 4-bedroom with four and half bathrooms
Worcester
10.0 out of 10, Exceptional, (12 reviews)
"10/10 great place to stay"
United States
Tyler B.
The price is AED 1,010
AED 1,871 total
includes taxes & fees
17 Jun - 18 Jun
Spacious 4-bedroom with four and half bathrooms
Terrace/patio

Stunning Lakefront Escape! Book Your Dream Getaway!

Stunning Lakefront Escape! Book Your Dream Getaway!
Woodstock
10.0 out of 10, Exceptional, (25 reviews)
"Welcoming host! Beautiful house with great amenities!"
United States
maria c.
The price is AED 1,488
AED 2,518 total
includes taxes & fees
15 Jun - 16 Jun
Stunning Lakefront Escape! Book Your Dream Getaway!
Property grounds

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 AED 1,102
AED 1,391 total
includes taxes & fees
26 Jun - 27 Jun
Family-friendly 2- Bedroom Webster Home w/Cozy Balcony
Dining

Clifford Luxury Retreat 3BR Self Check In Home

Clifford Luxury Retreat 3BR Self Check In Home
Northbridge
The price is AED 1,322
AED 1,576 total
includes taxes & fees
17 Jun - 18 Jun
Clifford Luxury Retreat 3BR Self Check In Home
Private kitchen

4-bedroom house in nice Holden with WiFi, AC

4-bedroom house in nice Holden with WiFi, AC
Holden
The price is AED 1,377
AED 2,077 total
includes taxes & fees
25 Jun - 26 Jun
4-bedroom house in nice Holden with WiFi, AC
TV, fireplace

Sleeps 15 • Pool • World Cup 2026 • Retreat

Sleeps 15 • Pool • World Cup 2026 • Retreat
Brimfield
10.0 out of 10, Exceptional, (34 reviews)
"We visited in December, so the pool was closed, but looked inviting even in the snow. The home was so warm and cozy and spacious. We loved our stay."
United States
Gina O.
The price is AED 3,636
AED 6,515 total
includes taxes & fees
19 Jun - 20 Jun
Sleeps 15 • Pool • World Cup 2026 • Retreat
Dining

Secluded 2-Acre Lakefront Home! Book Your Getaway!

Secluded 2-Acre Lakefront Home! Book Your Getaway!
Woodstock
9.8 out of 10, Exceptional, (84 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 1,837
AED 2,967 total
includes taxes & fees
21 Jun - 22 Jun
Secluded 2-Acre Lakefront Home! Book Your Getaway!
Property grounds

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!
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

Rodeway Inn Willington North

Rodeway Inn Willington North

8/10 Good
"For the price is just fine."
Susan 1-night trip
Posted 1 hour ago
Rodeway Inn Willington North

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