A river surrounded by autumn foliage.

Southbridge Vacation Rentals

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Check prices for these dates

In two weeks
Oct 2 - Oct 4
In two months
Nov 13 - Nov 15
In three months
Dec 11 - Dec 13
In four months
Jan 8 - Jan 10

Our top choices for Southbridge vacation rentals

Interior

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

Charming 1-bedroom apartment with AC & Breakfast in Sturbridge
Sturbridge
$118 nightly
The price is $132
Sep 25 - Sep 26
Total with taxes and fees
Charming 1-bedroom apartment with AC & Breakfast in Sturbridge
Exterior

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.
$166 nightly
The price is $188
Sep 21 - Sep 22
Total with taxes and fees
Wizard's Roost at Underhill Hollow
Exterior

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

Lakefront - King - PetsOK - W&D - Fire Pit - Kayak
Ashford
9.2 out of 10, Wonderful, (40 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.
$280 nightly
The price is $317
Sep 21 - Sep 22
Total with taxes and fees
Lakefront - King - PetsOK - W&D - Fire Pit - Kayak
Exterior

4. Dove Cabin up in the Trees

Dove Cabin up in the Trees
Holland
9.8 out of 10, Exceptional, (36 reviews)
"The owner was pleasant and accommodating "
United States
Maryann
$244 nightly
The price is $257
Sep 21 - Sep 22
Total with taxes and fees
Dove Cabin up in the Trees
Terrace/patio

5. 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, (49 reviews)
"Better than pictured. Beautiful lake and decks! Super comfortable living room furniture. Near great local restaurants."
United States
Julianne
$290 nightly
The price is $328
Sep 22 - Sep 23
Total with taxes and fees
Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake
Property grounds

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

Farm - Animals - Barn - Gazebo - Fire Pit - 2xKing
Willington
9.6 out of 10, Exceptional, (18 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
$180 nightly
The price is $204
Sep 23 - Sep 24
Total with taxes and fees
Farm - Animals - Barn - Gazebo - Fire Pit - 2xKing
Living area

7. 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
10.0 out of 10, Exceptional, (1 review)
"Cute place! Susan was a great host and the cabin was perfect for a qick getaway weekend and some reconnection with mother nature.."
United States
Jessica K.
$230 nightly
The price is $243
Sep 21 - Sep 22
Total with taxes and fees
Cozy 2-bedroom cabin in welcoming Holland with AC comfort at Mishnoah Retreat
Interior

8. 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.
$282 nightly
The price is $315
Sep 27 - Sep 28
Total with taxes and fees
Cozy Chic Countryside Haven - Sleeps 4 , Firepit
Interior

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

Modern 1-bedroom apartment in peaceful Sturbridge with AC
Sturbridge
7.0 out of 10, Good, (2 reviews)
"Clean place short drive to all Sturbridge attractions."
United States
Lynn M. T.
$115 nightly
The price is $128
Sep 21 - Sep 22
Total with taxes and fees
Modern 1-bedroom apartment in peaceful Sturbridge with AC
Interior

10. The Tree House at Underhill Hollow

The Tree House at Underhill Hollow
Thompson
9.4 out of 10, Exceptional, (42 reviews)
"Great space, lots of fun."
United States
Douglas C.
$171 nightly
The price is $194
Sep 21 - Sep 22
Total with taxes and fees
The Tree House at Underhill Hollow
Exterior

11. Treehouse - Countryside - Farm Animals - Fire Pit

Treehouse - Countryside - Farm Animals - Fire Pit
Willington
9.4 out of 10, Exceptional, (37 reviews)
"Beautiful farm that’s perfect little getaway for one weekend"
United States
Justyn M.
$285 nightly
The price is $323
Oct 20 - Oct 21
Total with taxes and fees
Treehouse - Countryside - Farm Animals - Fire Pit
Outdoor dining

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

Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD
Ashford
9.6 out of 10, Exceptional, (24 reviews)
"Place was really nice and in a location that made it easy to get back and forth to UCONN. "
United States
Jason C.
$229 nightly
The price is $260
Sep 21 - Sep 22
Total with taxes and fees
Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD
Property grounds

13. 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)
"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.
$198 nightly
The price is $221
Oct 6 - Oct 7
Total with taxes and fees
Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8
Property grounds

14. 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.
$166 nightly
The price is $188
Sep 27 - Sep 28
Total with taxes and fees
SteamPunk Bunk House and Intergalactic Way Station
Exterior

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

Charming 2-bedroom apartment in welcoming Putnam - 2nd Floor
Putnam
9.0 out of 10, Wonderful, (8 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.
$192 nightly
The price is $217
Sep 22 - Sep 23
Total with taxes and fees
Charming 2-bedroom apartment in welcoming Putnam - 2nd Floor
Living area

16. Clean & Cozy Private- 3 floor_R 4

Clean & Cozy Private- 3 floor_R 4
Union HIll
$88 nightly
The price is $101
Oct 16 - Oct 17
Total with taxes and fees
Clean & Cozy Private- 3 floor_R 4
Exterior

17. The Little Blue Bird

The Little Blue Bird
Willington
10.0 out of 10, Exceptional, (1 review)
"Great place! Great communication! Highly recommended for 1-2 people."
United States
Jeff G.
$144 nightly
The price is $163
Sep 28 - Sep 29
Total with taxes and fees
The Little Blue Bird
Property grounds

18. 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, (25 reviews)
"Nice place to stay a lot of family activities on the premises short distance to shopping and attractions"
United States
Andrew
$175 nightly
The price is $185
Sep 21 - Sep 22
Total with taxes and fees
Little House Inn - Private Home - Secluded - Ware - 2 bedroom, sleeps 6
Exterior detail

19. Cozy 1-bedroom cottage in serene Pomfret.

Cozy 1-bedroom cottage in serene Pomfret.
Pomfret
9.0 out of 10, Wonderful, (4 reviews)
"Great spot, clean and cozy."
United States
Bud n' Mary's Marina B.
$277 nightly
The price is $314
Sep 21 - Sep 22
Total with taxes and fees
Cozy 1-bedroom cottage in serene Pomfret.
Coffee/tea maker, fridge, microwave, oven

20. Breezy 4BR Worcester Home • Pet-Friendly • Summer Fun near I-290 & Parks 16-3

Breezy 4BR Worcester Home • Pet-Friendly • Summer Fun near I-290 & Parks 16-3
Worcester
10.0 out of 10, Exceptional, (2 reviews)
"Very nice stay. Plenty of space for the 7 of us that stayed, could have easily had 4 more. Recently refinished, so I think Jenny is still getting it all well stocked with kitchen wares. Only down side was window unit AC, which was a bit noisy when trying to watch TV (or for delicate sleepers)"
United States
Andrew O.
$364 nightly
The price is $417
Sep 28 - Sep 29
Total with taxes and fees
Breezy 4BR Worcester Home • Pet-Friendly • Summer Fun near I-290 & Parks 16-3
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

Holiday Inn Express & Suites Sturbridge by IHG

Holiday Inn Express & Suites Sturbridge by IHG

10/10 Excellent
"Staff is so friendly and professional! Property was clean!"
John 2-night trip
Posted 17 hours ago
Holiday Inn Express & Suites Sturbridge by IHG

Find out more about Southbridge

Everything you need to know about Southbridge vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Southbridge vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Southbridge vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Southbridge vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Southbridge. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Southbridge in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $128 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Southbridge rentals

At Expedia, we put the best Southbridge vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Southbridge rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Southbridge vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Southbridge. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

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 Upper Chapin Street 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 Windsor Court 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.