A river surrounded by autumn foliage.

Southbridge Vacation Rentals

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Check prices for these dates

In two weeks
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

Our top choices for Southbridge vacation rentals

A room with a blue wall, a mirror, a table with chairs, potted plants, and a Christmas tree.

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 CA $73
CA $113 total
includes taxes & fees
Sep 1 - Sep 2
Modern 1-bedroom apartment in peaceful Sturbridge with AC
A wooden cabin with a glass upper floor, surrounded by a forest.

2. Dove Cabin up in the Trees

Dove Cabin up in the Trees
Holland
9.6 out of 10, Exceptional, (35 reviews)
"The owner was pleasant and accommodating "
United States
Maryann
The price is CA $241
CA $356 total
includes taxes & fees
Aug 28 - Aug 29
Dove Cabin up in the Trees

3. Cozy 2-bedroom cabin in welcoming Holland with AC comfort at Mishnoah Retreat

Cozy 2-bedroom cabin in welcoming Holland with AC comfort at Mishnoah Retreat
Holland
The price is CA $235
CA $332 total
includes taxes & fees
Aug 28 - Aug 29
Cozy 2-bedroom cabin in welcoming Holland with AC comfort at Mishnoah Retreat
A wooden deck with outdoor furniture, overlooking a lake with boats and houses in the background.

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

Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake
Stafford
9.6 out of 10, Exceptional, (48 reviews)
"We had a great time swimming and kayaking. The house was spotless. Lake front with great parking."
United States
Christy
The price is CA $180
CA $454 total
includes taxes & fees
Sep 11 - Sep 12
Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake
A modern kitchen with white cabinets, a stainless steel refrigerator, and a dining area with a table and chairs.

5. Cozy Chic Countryside Haven - Sleeps 4 , Firepit

Cozy Chic Countryside Haven - Sleeps 4 , Firepit
Sturbridge
10.0 out of 10, Exceptional, (3 reviews)
"The place was immaculate, very large room, great kitchen, great bath, plenty of room for a family, quiet and secluded area few minutes away from town, outstanding communication with the property owner..true home away from home...Try it for yourself.."
United States
Giora Y.
The price is CA $281
CA $533 total
includes taxes & fees
Sep 13 - Sep 14
Cozy Chic Countryside Haven - Sleeps 4 , Firepit
A room with a sloped ceiling, wooden beams, a purple door, and a star decoration on the wall.

6. The Tree House at Underhill Hollow

The Tree House at Underhill Hollow
Thompson
9.4 out of 10, Exceptional, (40 reviews)
"Great space, lots of fun."
United States
Douglas C.
The price is CA $173
CA $266 total
includes taxes & fees
Aug 31 - Sep 1
The Tree House at Underhill Hollow
A red building with a colorful mural on the front, a covered porch, and a stone foundation.

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 CA $173
CA $259 total
includes taxes & fees
Aug 31 - Sep 1
Wizard's Roost 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, (17 reviews)
"Enjoyed our stay. Loved being out in the countryside "
United States
Pauline S.
The price is CA $173
CA $259 total
includes taxes & fees
Aug 28 - Aug 29
SteamPunk Bunk House and Intergalactic Way Station
A wooden cabin with a balcony and stairs, surrounded by trees.

9. Treehouse - Countryside - Farm Animals - Fire Pit

Treehouse - Countryside - Farm Animals - Fire Pit
Willington
9.4 out of 10, Exceptional, (37 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 CA $147
CA $367 total
includes taxes & fees
Aug 30 - Aug 31
Treehouse - Countryside - Farm Animals - Fire Pit
A wooden bench and a small wooden bridge in a natural setting with greenery and a stream.

10. 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, (9 reviews)
"Excellent communicative host with warm welcome and delightful amenities. Quiet neighborhood with plenty of parking."
United States
Pamela L.
The price is CA $206
CA $261 total
includes taxes & fees
Aug 26 - Aug 27
Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8
A group of people seated around a fire pit in a garden with a gazebo and trees in the background.

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

Farm - Animals - Barn - Gazebo - Fire Pit - 2xKing
Willington
9.6 out of 10, Exceptional, (17 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 CA $97
CA $303 total
includes taxes & fees
Sep 3 - Sep 4
Farm - Animals - Barn - Gazebo - Fire Pit - 2xKing
A room with a blue wall, a mirror, a table with chairs, potted plants, and a Christmas tree.

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

Charming 1-bedroom apartment with AC & Breakfast in Sturbridge
Sturbridge
The price is CA $83
CA $199 total
includes taxes & fees
Aug 26 - Aug 27
Charming 1-bedroom apartment with AC & Breakfast in Sturbridge
A small, single-story cabin with a porch and a small deck, surrounded by trees and a lake.

13. Lakefront - King - PetsOK - W&D - Fire Pit - Kayak

Lakefront - King - PetsOK - W&D - Fire Pit - Kayak
Ashford
9.2 out of 10, Wonderful, (39 reviews)
"We had a nice stay in this cabin by the lake. It was close to UCONN so the convenience of the location was wonderful. "
United States
Jennifer P.
The price is CA $252
CA $503 total
includes taxes & fees
Aug 29 - Aug 30
Lakefront - King - PetsOK - W&D - Fire Pit - Kayak
A house with a white porch, a black door, and a window with a white frame.

14. 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 CA $337
CA $433 total
includes taxes & fees
Aug 28 - Aug 29
Cozy 1-bedroom cottage in serene Pomfret.
A two-story house with a front porch, stone steps, and a driveway.

15. 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, (6 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 CA $174
CA $311 total
includes taxes & fees
Sep 22 - Sep 23
Charming 2-bedroom apartment in welcoming Putnam - 2nd Floor
A grassy outdoor area with a hammock, chairs, and a stone wall.

16. 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, (24 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 CA $253
CA $301 total
includes taxes & fees
Aug 27 - Aug 28
Little House Inn - Private Home - Secluded - Ware - 2 bedroom, sleeps 6

17. 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 CA $317
CA $362 total
includes taxes & fees
Aug 31 - Sep 1
Cottage by the Castle – Downtown Spencer
A deck with red Adirondack chairs, a grill, and a view of trees and sunset.

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

Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD
Ashford
9.6 out of 10, Exceptional, (23 reviews)
"Place was really nice and in a location that made it easy to get back and forth to UCONN. "
United States
Jason C.
The price is CA $221
CA $464 total
includes taxes & fees
Aug 26 - Aug 27
Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD
A compact RV interior with a kitchenette, a dining area, and a seating area with a dog.

19. Serenity meets Taradise

Serenity meets Taradise
Union
The price is CA $149
CA $239 total
includes taxes & fees
Sep 7 - Sep 8
Serenity meets Taradise
A dining area with a high ceiling, skylights, and a view of the outdoors.

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

Secluded 2-Acre Lakefront Home! Book Your Getaway!
Woodstock
9.8 out of 10, Exceptional, (88 reviews)
"The hosts were welcoming and the house was very clean and a great place to stay!"
United States
Emma S.
The price is CA $658
CA $1,059 total
includes taxes & fees
Sep 1 - Sep 2
Secluded 2-Acre Lakefront Home! Book Your Getaway!
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

Hampton Inn & Suites Worcester

Hampton Inn & Suites Worcester

10/10 Excellent
"Clean and convenient"
Lisa 1-night trip
Posted 1 hour ago
Hampton Inn & Suites Worcester

Find out more about Southbridge

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Southbridge. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find vacation rentals in Southbridge?

Yes, we give you a choice of vacation rentals in Southbridge close to Walcott Street Playground, or you can select a more secluded option if you'd like a relaxing place to stay. Our travelers 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 vacation rentals in Southbridge?

Impressive Unique Waterfront Pool Resort Country Estate: This highly rated vacation home rental in Southbridge is located on a lake and has an outdoor pool, a fireplace, and a barbecue grill 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 you can cook with friends or family. It offers a patio, a garden, and a selection of games so you can immerse yourself in your vacation.

How many vacation rentals are there in Southbridge?

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

What’s there to see and do in Southbridge?

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

What’s a vacation rental in Southbridge like?

Vacation rentals are private properties where you can stay for a few weeks or just a few days in Southbridge. Vacation rentals feature amenities such as kitchens and laundry facilities so you'll feel just like you're staying in your own home. If you're concerned about cleanliness, a vacation rental can offer a sense of privacy away from public hotel elevators and busy concierge desks while still allowing you to travel. You'll also have more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a popular choice for a family trip or a small group gathering.