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Compare 75 Vacation Homes in Southbridge with updated reviews, rates, and availability.

completely renovated 3 bedroom, 2 bath overlooking idyllic lake whittemore
Property grounds
completely renovated 3 bedroom, 2 bath overlooking idyllic lake whittemore
10.0 out of 10, Exceptional, (180)
"Quiet cozy and needs a bigger television or tvs in each room "
completely renovated 3 bedroom, 2 bath overlooking idyllic lake whittemore
Enjoy the Fun of a Lakefront GetAway, While Only Minutes from Local Attractions!
Welcome to family fun and dining, directly on the lake!
Enjoy the Fun of a Lakefront GetAway, While Only Minutes from Local Attractions!
9.8 out of 10, Exceptional, (102)
"Very nice, well equipped, absolutely beautiful view!!!!!!"
Enjoy the Fun of a Lakefront GetAway, While Only Minutes from Local Attractions!
Large relaxing house in 25 acres of private woods with lake access.
Dining
Large relaxing house in 25 acres of private woods with lake access.
10.0 out of 10, Exceptional, (16)
"Excellent home in the woods. All as advertised, my family and I thoroughly enjoyed it. Communication with the owner was excellent. 10/10, we’ll be back next time we’re in the area"
Large relaxing house in 25 acres of private woods with lake access.
Cozy home 5 minutes to shopping center, HC college, 2 kitchens, 2 living rooms
Exterior
Cozy home 5 minutes to shopping center, HC college, 2 kitchens, 2 living rooms
10.0 out of 10, Exceptional, (1)
"Everything was spotlessly clean. The beds were comfortable, and every convenience was considered. Excellent place for a larger group—we needed 4 bedrooms—coming to town to move my son in to WPI for college. Would strongly recommend!!!"
Cozy home 5 minutes to shopping center, HC college, 2 kitchens, 2 living rooms
The Tree House at Underhill Hollow
Exterior
The Tree House at Underhill Hollow
9.4 out of 10, Exceptional, (13)
"Michael has done a fantastic job not only providing a comfortable and beautiful accommodation, but his creativity and skill shine in the many wonderful contraptions, puzzles and surprises around the property. A great place to stay for the gorgeous CT scenery, even better for the many opportunities of adventure scattered around the grounds. Will definitely recommend this to friends and family, and hope to come back in the future to find anything we missed!"
The price is SAR 451
SAR 702 total
includes taxes & fees
15 Dec - 16 Dec
The Tree House at Underhill Hollow
Breathtaking Lakefront Property! Cozy house! Special off-season rates!
Exterior
Breathtaking Lakefront Property! Cozy house! Special off-season rates!
10.0 out of 10, Exceptional, (9)
"Beautifully appointed home on a beautiful lake in Woodstock, CT. We enjoyed kayaking on the lake, visiting nearby orchards and hiking the many scenic trails nearby. Many great restaurants in the area as well. Although we did not partake, there is a great rail trail nearby for hiking, walking, etc. The home listing is very accurate, the kitchen is well equipped, and the cleanliness of the home is top notch. In addition, the hosts Heather and Dan, were very responsive and were...
The price is SAR 1,108
SAR 2,029 total
includes taxes & fees
15 Dec - 16 Dec
Breathtaking Lakefront Property! Cozy house! Special off-season rates!
Charming 3 bedroom home Centrally located in Worcester
Living area
Charming 3 bedroom home Centrally located in Worcester
9.0 out of 10, Wonderful, (2)
"The home is very comfortable and good neighborhood.Bed was comfy and beding too.Would return again!"
Charming 3 bedroom home Centrally located in Worcester
Secluded 2-acre Lake Front Home! Special off-season rates!
Exterior
Secluded 2-acre Lake Front Home! Special off-season rates!
9.8 out of 10, Exceptional, (59)
"The house is in a beautiful location and is setup wonderfully to joyfully cook a big meal with a group of people. The house is comfortable and inviting, if a bit worn down (chipping paint, rust, and some dusty shelves). The beds are comfortable as are the sitting and living rooms. The jetted bathtub in the pictures was out of order and there are instructions not to use the wood stoves. The hosts have very distinct instructions and their personality was clearly showcased. "
The price is SAR 1,108
SAR 2,029 total
includes taxes & fees
15 Dec - 16 Dec
Secluded 2-acre Lake Front Home! Special off-season rates!
Wizard's Roost at Underhill Hollow
Exterior
Wizard's Roost at Underhill Hollow
10.0 out of 10, Exceptional, (5)
"Cute and fun spot in the country. Very quiet. Room was clean and had everything we needed. Beds comfy. Nice property. Very friendly owner. A bit dark at the top of the driveway if you come in at night watch for the turn. "
The price is SAR 413
SAR 637 total
includes taxes & fees
15 Dec - 16 Dec
Wizard's Roost at Underhill Hollow
Spacious and luxurious 3-bedroom home w/jetted bathtub
Interior
Spacious and luxurious 3-bedroom home w/jetted bathtub
10.0 out of 10, Exceptional, (3)
"Only caveats are the air conditioning is primitive"
Spacious and luxurious 3-bedroom home w/jetted bathtub
Lake House in Sturbridge w/All the Views!
House from above the lake
Lake House in Sturbridge w/All the Views!
9.8 out of 10, Exceptional, (6)
"We had a great time in Sturbridge. Can't beat the location of this house - it's absolutely beautiful, and very close to Old Sturbridge Village and a cute coffee shop we frequented during the long weekend. Everything was nice and clean, the hot tub was great, and it was easy to check in. The beds are comfortable and it was nice to not have to worry about the linens upon checkout. The host replied super promptly when we had questions about the location of trash/recycling bins, and when there was...
The price is SAR 2,048
SAR 3,571 total
includes taxes & fees
18 Nov - 19 Nov
Lake House in Sturbridge w/All the Views!
Full family home 200 ft from the lake shore. Dog friendly!
Exterior
Full family home 200 ft from the lake shore. Dog friendly!
10.0 out of 10, Exceptional, (4)
"The house is beautiful, comfortable and spotless. "
The price is SAR 1,147
SAR 2,193 total
includes taxes & fees
2 Dec - 3 Dec
Full family home 200 ft from the lake shore. Dog friendly!
Full House/Heart of Worcester
Exterior detail
Full House/Heart of Worcester
The price is SAR 545
SAR 1,329 total
includes taxes & fees
18 Nov - 19 Nov
Full House/Heart of Worcester
Spacious luxury 3 bedroom apartment
living room with huge TV
Spacious luxury 3 bedroom apartment
8.0 out of 10, Very Good, (2)
"Came from out of town with friends to enjoy a music festival at the Palladium. Location was easy to find and accesible to shops/food. Apartment was easy to access around back side. In our case we walked up the driveway as the gate was locked. Safe second floor apartment. Bed were clean, and rooms spacious. Only thing that was inconvenient the missing handle from the freezer door. "
Spacious luxury 3 bedroom apartment
Beautiful Colonial Home in a Peaceful Setting Bordering Natchaug State Forest
Exterior
Beautiful Colonial Home in a Peaceful Setting Bordering Natchaug State Forest
10.0 out of 10, Exceptional, (49)
"5 of us stayed here for a week while we were at an event nearby. The place is gorgeous, huge, impecably clean, and for our purposes very convenient. We particularly appreciated the nice touches of a bottle of wine and some snacks, and the large and very functional washing machine/dryer setup, We’re immediately trying to rebook for a trip next year!. We met the host once during our stay and they delightfully gave us a tour and he made sure everything was going well. Lovely to have a VRBO...
Beautiful Colonial Home in a Peaceful Setting Bordering Natchaug State Forest
"Duck Rock" Lakefront House with 200' Private Waterfront
Sunset View from Large Screened Deck
"Duck Rock" Lakefront House with 200' Private Waterfront
10.0 out of 10, Exceptional, (15)
"Loved the house"
"Duck Rock" Lakefront House with 200' Private Waterfront
Cheerful 3-BR 2-full BR home close to Downtown
Living area
Cheerful 3-BR 2-full BR home close to Downtown
8.6 out of 10, Excellent, (7)
"This was a great stay for our family and father-in-law for a family wedding. The property is well updated and communication with property management was excellent. The property does not have a dishwasher, which I missed when booking, but it was not a dealbreaker by any means. The neighborhood was quiet for the most part, and street parking was not an issue. There is a washer and dryer onsite, but it is not inside the home, so definitely ask the host for the information upon arrival!"
Cheerful 3-BR 2-full BR home close to Downtown
Quintessential New England Home w/ Patio & Grill!
Putnam Vacation Rental | 5BR | 2BA | 2,363 Sq Ft | 3 Steps Required
Quintessential New England Home w/ Patio & Grill!
2.0 star property
10.0 out of 10, Exceptional, (1)
"House was great, exactly as described and shown. If needed lodging while in the area, choose this rental."
Quintessential New England Home w/ Patio & Grill!
Cozy 3-bed 1.5 baths 1 mile from UConn campus. WiFi AC Patio Kitchen Dining room
Exterior
Cozy 3-bed 1.5 baths 1 mile from UConn campus. WiFi AC Patio Kitchen Dining room
2.0 star property
Cozy 3-bed 1.5 baths 1 mile from UConn campus. WiFi AC Patio Kitchen Dining room
Cozy 3 bedroom home
Exterior
Cozy 3 bedroom home
10.0 out of 10, Exceptional, (3)
"Great location and a nice small place for the boys. It was great since we spent Friday night at a wedding and was nice to have a place so we didn’t have to drive back home. A+ experience. "
Cozy 3 bedroom home
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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Other property types in Southbridge

Impressive Unique Waterfront Pool Resort Country Estate
YOUR OWN HEATED POOL
Impressive Unique Waterfront Pool Resort Country Estate
9.8 out of 10, Exceptional, (53)
"Absolutely perfect. Gorgeous property, gorgeous house. Every amenity. All the little touches are amazing. It is a work of art. Appreciate the host and her attention to detail. She made us feel welcome. Could not have been better. Thank you so much."
Impressive Unique Waterfront Pool Resort Country Estate
One Bedroom Fully Furnished Apartment
Living Room
One Bedroom Fully Furnished Apartment
9.8 out of 10, Exceptional, (11)
"The apartment is nice and just as pictured, and we had a comfortable stay. What's not clear from the listing is that it isn't in a residential neighborhood but in the middle of a shopping center. That wasn't really a problem for us, but it was a little surprising."
One Bedroom Fully Furnished Apartment
Wrecked at Ron’s
Terrace/patio
Wrecked at Ron’s
10.0 out of 10, Exceptional, (6)
"House is spacious and comfortable with a fully equipped kitchen that has everything you need. Beds were comfortable and bathrooms were conveniently located on both floors. Everything was clean and tidy. It's clear Ron is doing continuous updates to the property, but that didn't bother us at all. Location is very peaceful with gorgeous views and spectacular sunrises and sunsets. Ron is right on site and readily available if needed. We'd definitley stay again."
Wrecked at Ron’s
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.