A river surrounded by autumn foliage.

Southbridge Holiday Rentals

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Check prices for these dates

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

Our top choices for Southbridge holiday rentals

Interior

1. Modern 1-bedroom apartment in peaceful Sturbridge with AC

Modern 1-bedroom apartment in peaceful Sturbridge with AC
Sturbridge
8.0 out of 10, Very good, (1 review)
"Clean place short drive to all Sturbridge attractions."
United States
Lynn M. T.
The price is HK$463
HK$692 total
includes taxes & fees
10 Aug - 11 Aug
Modern 1-bedroom apartment in peaceful Sturbridge with AC
Exterior

2. Dove Cabin up in the Trees

Dove Cabin up in the Trees
Holland
9.8 out of 10, Exceptional, (32 reviews)
"Sue is a great host, making necessary adjustments to suit the circumstances, generous and flexible. The dove cabin is so sweet, comfortable beds, cozy stove and fully equipped kitchen. And lovely porch! There’s a really cool swing on the way down to a peaceful pond!"
United States
kathryn m.
The price is HK$1,376
HK$2,010 total
includes taxes & fees
31 Jul - 1 Aug
Dove Cabin up in the Trees
Interior

3. 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 HK$988
HK$1,518 total
includes taxes & fees
3 Aug - 4 Aug
The Tree House at Underhill Hollow
Interior

4. Charming 1-bedroom apartment with AC & Breakfast in Sturbridge

Charming 1-bedroom apartment with AC & Breakfast in Sturbridge
Sturbridge
The price is HK$470
HK$1,130 total
includes taxes & fees
7 Aug - 8 Aug
Charming 1-bedroom apartment with AC & Breakfast in Sturbridge
Property grounds

5. Farm - Animals - Barn - Gazebo - Fire Pit - 2xKing

Farm - Animals - Barn - Gazebo - Fire Pit - 2xKing
Willington
9.8 out of 10, Exceptional, (16 reviews)
"We loved the ambience, super quiet, my kids love the animals The host was super comunicative making sure we was good during our stay"
United States
Silvino
The price is HK$652
HK$1,809 total
includes taxes & fees
3 Aug - 4 Aug
Farm - Animals - Barn - Gazebo - Fire Pit - 2xKing
Terrace/patio

6. Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake

Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake
Stafford
9.8 out of 10, Exceptional, (46 reviews)
"We had a great time swimming and kayaking. The house was spotless. Lake front with great parking."
United States
Christy
Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake
Exterior

7. 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 HK$988
HK$1,474 total
includes taxes & fees
13 Aug - 14 Aug
Wizard's Roost at Underhill Hollow
Property grounds

8. 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 HK$988
HK$1,474 total
includes taxes & fees
2 Aug - 3 Aug
SteamPunk Bunk House and Intergalactic Way Station
Exterior

9. Treehouse - Countryside - Farm Animals - Fire Pit

Treehouse - Countryside - Farm Animals - Fire Pit
Willington
9.4 out of 10, Exceptional, (35 reviews)
"Loved my "staycation" at the Tree house. I just needed a couple of days to relax. Carmen and Joe are very friendly. Loved the location, the scenery and the animals. Great place to unwind. Would love to go back some time, maybe in the fall, I bet it's beautiful."
United States
mythra 7.
The price is HK$1,423
HK$2,821 total
includes taxes & fees
16 Aug - 17 Aug
Treehouse - Countryside - Farm Animals - Fire Pit
Exterior

10. The Carriage House at Chaprae Hall

The Carriage House at Chaprae Hall
Killingly
10.0 out of 10, Exceptional, (33 reviews)
"Just as advertised clean and comfortable, thank you gentlemen. Keep up the good work. :)"
United States
Herbert
The price is HK$863
HK$1,608 total
includes taxes & fees
26 Aug - 27 Aug
The Carriage House at Chaprae Hall
Property grounds

11. 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 HK$1,390
HK$1,746 total
includes taxes & fees
2 Aug - 3 Aug
Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8
3 bedrooms, iron/ironing board, free WiFi, bed sheets

12. Apartment in town center #1

Apartment in town center #1
West Brookfield
8.8 out of 10, Excellent, (28 reviews)
"Stayed here to visit Treehouse brewing with some friends and it was perfect. "
United States
Chris G.
Apartment in town center #1
Smart TV

13. Serenity meets Taradise

Serenity meets Taradise
Union
The price is HK$847
HK$1,356 total
includes taxes & fees
2 Aug - 3 Aug
Serenity meets Taradise
Living area

14. Clean & Cozy Private- 3 floor_R 4

Clean & Cozy Private- 3 floor_R 4
Union HIll
The price is HK$536
HK$793 total
includes taxes & fees
2 Aug - 3 Aug
Clean & Cozy Private- 3 floor_R 4
Interior

15. Trainmaster's Inn - Caboose

Trainmaster's Inn - Caboose
Palmer
9.4 out of 10, Exceptional, (10 reviews)
"A great stay in a vintage RR caboose. Thanks to everyone at Trainmasters Inn!"
United States
Edward L.
The price is HK$1,176
HK$2,715 total
includes taxes & fees
2 Aug - 3 Aug
Trainmaster's Inn - Caboose
Interior

16. Spacious Massachusetts Apartment #2

Spacious Massachusetts Apartment #2
West Brookfield
9.2 out of 10, Wonderful, (31 reviews)
"Really a cute place to stay, very clean and comfortable "
United States
Michelle J.
Spacious Massachusetts Apartment #2
Smart TV

17. Newly Renovated 4BR Worcester Home • Pet-Friendly • Near I-290 & Park 16-2

Newly Renovated 4BR Worcester Home • Pet-Friendly • Near I-290 & Park 16-2
Worcester
10.0 out of 10, Exceptional, (6 reviews)
"Clean, perfect, had everything we needed for a quick stay "
United States
Sierra M.
The price is HK$1,727
HK$3,780 total
includes taxes & fees
3 Aug - 4 Aug
Newly Renovated 4BR Worcester Home • Pet-Friendly • Near I-290 & Park 16-2
Interior

18. Modern Stay 3BR Worcester Apt • FREE Parking near Clark University & I-290 4/1

Modern Stay 3BR Worcester Apt • FREE Parking near Clark University & I-290 4/1
Main South
10.0 out of 10, Exceptional, (1 review)
The price is HK$1,260
HK$2,968 total
includes taxes & fees
3 Aug - 4 Aug
Modern Stay 3BR Worcester Apt • FREE Parking near Clark University & I-290 4/1
Exterior

19. Charming 2-bedroom apartment in welcoming Putnam - 2nd Floor

Charming 2-bedroom apartment in welcoming Putnam - 2nd Floor
Putnam
8.8 out of 10, Excellent, (5 reviews)
"Clean place, easy check-in and comfortable place. We appreciated the coffee and water, microwave and clean towels. We would stay here again!! Thank you!! "
United States
Lucy L.
The price is HK$1,249
HK$2,099 total
includes taxes & fees
11 Aug - 12 Aug
Charming 2-bedroom apartment in welcoming Putnam - 2nd Floor
Exterior detail

20. Cozy 1-bedroom cottage in serene Pomfret.

Cozy 1-bedroom cottage in serene Pomfret.
Pomfret
10.0 out of 10, Exceptional, (2 reviews)
"I had a lovely stay at the cottage! It was clean, comfortable, and quiet with a great view. The hosts were very helpful."
United States
Aaron H.
The price is HK$1,921
HK$2,429 total
includes taxes & fees
12 Aug - 13 Aug
Cozy 1-bedroom cottage in serene Pomfret.
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

Scottish Inn Sturbridge

Scottish Inn Sturbridge

10/10 Excellent
"This was a basic motel with basic amenities. What set it aside was the cleanliness of the property and kindness of the staff. I was grateful to stay at an affordable hotel that felt safe and welcoming. So glad I chose the Scottish Inn. If you are looking for a comfortable place to stay and you are not expecting resort amenities then this is a great choice in Sturbridge."
Russell 1-night trip
Posted 1 hour ago
Scottish Inn Sturbridge

Find out more about Southbridge

Search for holiday rentals in Southbridge on Expedia! You can easily find your home rentals, villas, holiday apartments in Southbridge using one of the methods below:

  • View our selection of featured holiday rentals in Southbridge
  • Use the map to find apartments and other holiday homes in the Southbridge neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Southbridge while they last

Look no further and take a look at our great range of rental properties in Southbridge!

Frequently asked questions

Can I find holiday rentals in Southbridge?

Yes, there are holiday rentals in Southbridge close to Walcott Street Playground, or you can select a more secluded option if you're looking for a relaxing stay. Our travellers say Southbridge has a good selection of restaurants and the bars. Make sure you have time to check out the spas while you're in the area.

What are some of the best holiday rentals that Southbridge has to offer?

Impressive Unique Waterfront Pool Resort Country Estate: This highly rated holiday home rental in Southbridge is located on a lake, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a patio, a garden and a selection of games so that you can immerse yourself in your holiday.

How many holiday rentals are there in Southbridge?

With 3 Expedia holiday rentals, you're guaranteed to find just the right place for your Southbridge stay.

What’s there to see and do in Southbridge?

Windsor Court Historic District and Westville Recreation Area are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Walcott Street Playground. While here, Upper Chapin Street Historic District and High School Street Historic District are other places worth a visit.

What’s a holiday rental in Southbridge like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Southbridge. Holiday rentals offer extras such as WiFi and washers and dryers so you'll feel right at home. If you're concerned about a sanitised environment, a holiday rental can provide a sense of security away from public hotel lifts and bustling concierge desks while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a popular option for family trips.