A river with a waterfall, surrounded by autumn-colored trees.

Holiday Homes in Southborough

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Check prices for these dates

In two weeks
25 Sept - 27 Sept
In two months
6 Nov - 8 Nov
In three months
4 Dec - 6 Dec
In four months
1 Jan - 3 Jan

Our top choices for Southborough holiday homes

An outdoor patio with a table, chairs, a grill, and a gazebo.

1. Private Garden Estate, Jacuzzi, Cinema & Games

Private Garden Estate, Jacuzzi, Cinema & Games
Southborough
10.0 out of 10, Exceptional, (1 review)
"Jillian provided a wonderful home to stay in. Quiet areas are always a plus. Communications were quick and properly responsive. Very comfortable home. Pool table and pinball made for enjoyable evenings."
United States
John R.
The price is €419
includes taxes & fees
20 Sept - 21 Sept
Private Garden Estate, Jacuzzi, Cinema & Games
A modern kitchen with white cabinets, a central island, a microwave, and a stove.

2. totally remodeled house with fitness room, close to Boston and Worcester

totally remodeled house with fitness room, close to Boston and Worcester
Framingham
9.4 out of 10, Exceptional, (15 reviews)
"Nicely located in neighbor with easy access to highways and walking distance to coffee shop this single home is perfect for being near Boston. Space is comfortable with all the comforts of home. "
United States
Karyn V.
The price is €291
includes taxes & fees
22 Sept - 23 Sept
totally remodeled house with fitness room, close to Boston and Worcester
A modern kitchen with white cabinets, stainless steel appliances, and a wooden floor.

3. Charming 3-bedroom house in delightful Ashland for your getaway

Charming 3-bedroom house in delightful Ashland for your getaway
Ashland
9.4 out of 10, Exceptional, (3 reviews)
"This is our second stay here and both times have been good. The house is quiet, even for it being on a well traveled road. "
United States
John W.
The price is €254
includes taxes & fees
22 Sept - 23 Sept
Charming 3-bedroom house in delightful Ashland for your getaway
A bedroom with a large mirror, a bed with floral bedding, a standing lamp, and a window with curtains.

4. Beautiful & Cozy 2 BR/ 2Beds/ Netflix/Alexa/Roku.

Beautiful & Cozy 2 BR/ 2Beds/ Netflix/Alexa/Roku.
Shrewsbury
9.4 out of 10, Exceptional, (36 reviews)
"Lovely and great location "
United States
Kimberlee K.
Beautiful & Cozy 2 BR/ 2Beds/ Netflix/Alexa/Roku.
A modern kitchen with white cabinetry, a built-in oven, and a dining area with a table and chairs.

5. Newly Renovated beautiful 3-Bed 2-Bath Home with Easy Airport Access

Newly Renovated beautiful 3-Bed 2-Bath Home with Easy Airport Access
Framingham
9.6 out of 10, Exceptional, (30 reviews)
"Perfect place to stay. Clean and has everything you need. Would recommend anyone to stay here. "
United States
Michelle M.
The price is €326
includes taxes & fees
20 Sept - 21 Sept
Newly Renovated beautiful 3-Bed 2-Bath Home with Easy Airport Access
A modern living room with a blue sofa, a leather armchair, and a patterned rug.

6. Luxury Boston Ranch –Sleeps 8|Pet+|Heated pool

Luxury Boston Ranch –Sleeps 8|Pet+|Heated pool
Framingham
10.0 out of 10, Exceptional, (6 reviews)
"Very nice"
United States
Tricia S.
The price is €561
includes taxes & fees
14 Sept - 15 Sept
Luxury Boston Ranch –Sleeps 8|Pet+|Heated pool
A modern kitchen with white cabinets, a central island with bar stools, a large window, and a dark ceiling beam.

7. Spacious 5 Bedroom Retreat • Free Parking • Pet Friendly• Greater Boston

Spacious 5 Bedroom Retreat • Free Parking • Pet Friendly• Greater Boston
Framingham
10.0 out of 10, Exceptional, (5 reviews)
"The house was nice. The beds were very comfortable. The house was close to everything. Check-in and check-out process was easy."
United States
Christina S.
The price is €512
includes taxes & fees
14 Sept - 15 Sept
Spacious 5 Bedroom Retreat • Free Parking • Pet Friendly• Greater Boston
A spacious living area with a large sectional sofa, a glass coffee table, and a view of the outdoors through large windows.

8. Welcome in this charming one bedroom apartment located in Westwood. WorldCup2026

Welcome in this charming one bedroom apartment located in Westwood. WorldCup2026
Westwood
10.0 out of 10, Exceptional, (4 reviews)
"Easy-to-find location and charming accommodations. Everything was organized well and very clean. Would highly recommend this listing."
United States
Eva O.
The price is €235
includes taxes & fees
16 Sept - 17 Sept
Welcome in this charming one bedroom apartment located in Westwood. WorldCup2026
A two-story house with a front porch and a garden with purple flowers.

9. ✨Private Studio w/ Loft Center Historic Carlisle✨

✨Private Studio w/ Loft Center Historic Carlisle✨
Carlisle
9.4 out of 10, Exceptional, (36 reviews)
"Wonderful stay"
United States
Brent H.
The price is €170
includes taxes & fees
9 Sept - 10 Sept
✨Private Studio w/ Loft Center Historic Carlisle✨
A compact, modern laundry room with a built-in washer and dryer, a small storage cabinet, and a tiled floor.

10. 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 €230
includes taxes & fees
9 Sept - 10 Sept
Angel Sky Challenge
A bar area with a counter, two green chairs, a refrigerator, and a neon sign.

11. Game Room + Bar Lounge, 35 Min to Boston

Game Room + Bar Lounge, 35 Min to Boston
Worcester
Game Room + Bar Lounge, 35 Min to Boston
A modern kitchen with white cabinets, a marble countertop, and pendant lighting.

12. Modern Upper-Level Oasis, Minutes to Boston.

Modern Upper-Level Oasis, Minutes to Boston.
Norwood
9.8 out of 10, Exceptional, (8 reviews)
"Cute, welcoming, and everything we needed. Host was very responsive and we had a blast."
United States
Travis B.
The price is €354
includes taxes & fees
9 Sept - 10 Sept
Modern Upper-Level Oasis, Minutes to Boston.
A living room with a brown leather sofa, two green pillows, and a brown throw blanket. There are two windows with white blinds, and a small table with a plant.

13. Cozy house close to Brandeis, Bentley, Moody St

Cozy house close to Brandeis, Bentley, Moody St
South Side
9.2 out of 10, Wonderful, (7 reviews)
"We enjoy our stayed at the place.it’s nice and clean."
United States
Gabriel C.
Cozy house close to Brandeis, Bentley, Moody St
A modern kitchen with a stainless steel refrigerator, double sink, and wooden flooring.

14. Spacious 4-bedroom with four and half bathrooms

Spacious 4-bedroom with four and half bathrooms
Worcester
10.0 out of 10, Exceptional, (18 reviews)
"Perfect location"
United States
Harmony F.
The price is €434
includes taxes & fees
9 Sept - 10 Sept
Spacious 4-bedroom with four and half bathrooms
A hallway with a wooden floor, white walls, and a black shelving unit with decorative items.

15. Boston College Room conveniently near Harvard & BC

Boston College Room conveniently near Harvard & BC
Brighton
9.4 out of 10, Exceptional, (32 reviews)
"Over all fine place for a few day stay"
United States
jeannine g.
Boston College Room conveniently near Harvard & BC
A modern kitchen with a central island, stainless steel appliances, and green bar stools.

16. Lake Access 4 Bed 3 Full Bath

Lake Access 4 Bed 3 Full Bath
Billerica
9.8 out of 10, Exceptional, (23 reviews)
"The house was perfect for us! Sparkling clean and comfortable. We really enjoyed staying here and would stay again for sure!"
United States
Diane B.
The price is €676
includes taxes & fees
9 Sept - 10 Sept
Lake Access 4 Bed 3 Full Bath
A modern kitchen with white cabinetry, a large island, and pendant lighting.

17. Modern Farmhouse Close to Mt. Wachusett

Modern Farmhouse Close to Mt. Wachusett
Holden
Modern Farmhouse Close to Mt. Wachusett
A pool table in a room with a high ceiling and exposed ductwork.

18. Entire home in Sterling, Massachusetts, United States

Entire home in Sterling, Massachusetts, United States
Sterling
Entire home in Sterling, Massachusetts, United States
A kitchen with a granite countertop, stainless steel sink, and dishwasher. There is a window with a view of greenery outside.

19. Lakeview Getaway with Hot Tub

Lakeview Getaway with Hot Tub
Billerica
9.0 out of 10, Wonderful, (2 reviews)
"Great stay!"
United States
KrackleJak
The price is €546
includes taxes & fees
21 Sept - 22 Sept
Lakeview Getaway with Hot Tub
A modern kitchen with white cabinets, stainless steel appliances, and a central island with bar stools.

20. 4-bedroom house in nice Holden with WiFi, AC

4-bedroom house in nice Holden with WiFi, AC
Holden
10.0 out of 10, Exceptional, (1 review)
"The house was located in a quiet, nice, pleasant, neighborhood. The rooms were spacious and comfortable. The house was very clean and the beds were comfortable. The house was located near all kinds of stores, pharmacy’s, and good restaurants. I’d I had to make a negative comment it would be that all the bedrooms were on the second floor which was tough for two of our party. The property owner was quick to respond to questions we had. Overall, a very pleasant stay."
United States
Samantha R.
4-bedroom house in nice Holden with WiFi, AC
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 Southborough Hotel Reviews

Aloft by Marriott Lexington

Aloft by Marriott Lexington

8/10 Good
"Very close to Hanscom airfield great location for an early morning departure"
Jennifer 1-night trip
Posted 5 hours ago
Aloft by Marriott Lexington

Find out more about Southborough

Southborough Holiday Homes information

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