Southborough, MA Vacation Homes from ￥38,389

Southborough Vacation Homes
United States of America
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Our top choices for Southborough vacation homes

A modern kitchen with white cabinetry, a built-in oven, and a dining area with a table and chairs.

A kitchen drawer with a variety of utensils neatly organized.

A modern living room with a flat-screen TV, a glass coffee table, and a seating area with white sofas.

1. 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, (35 reviews)

9.6/10

Exceptional

(35 reviews)

"We had a great stay."

Jessica D.

The price is ￥36,569

￥36,569

￥61,078 total

includes taxes & fees

Nov 3 - Nov 4

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

A modern kitchen with white cabinets, a central island, a microwave, and a stove.

A bedroom with a wooden bed, grey bedding, and a beige throw blanket.

A living room with a sectional sofa, a single chair, a coffee table, and a flat-screen TV mounted on the wall.

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

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

Framingham

9.2 out of 10, Wonderful, (17 reviews)

9.2/10

Wonderful

(17 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. "

Karyn V.

The price is ￥28,296

￥28,296

￥50,138 total

includes taxes & fees

Nov 8 - Nov 9

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

A modern kitchen with white cabinets, a central island with bar stools, a large window, and a dark ceiling beam.

A living room with a sofa, a coffee table, and a TV. There is a window with curtains, a plant, and a chandelier.

A modern living room with a white sofa, a blue armchair, a coffee table, and a TV mounted on the wall.

A living room with a sofa, a blue armchair, a coffee table, a TV, and a painting on the wall.

3. 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)

10/10

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."

Christina S.

The price is ￥48,901

￥48,901

￥85,936 total

includes taxes & fees

Oct 29 - Oct 30

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

A modern living room with a blue sofa, a leather armchair, and a patterned rug.

A room with a blue door, a white wall, and a large window. There are two wicker chairs and a small table.

A room with a bunk bed, a desk, a chair, and a window with a view.

A modern living room with a blue sofa, two armchairs, a coffee table, and a floor lamp. There is a large window with curtains, a potted plant, and a wall-mounted air conditioning unit.

4. 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)

10/10

Exceptional

(6 reviews)

"Very nice"

Tricia S.

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

A spacious living room with wooden beams, a sliding glass door to a patio, and a cozy seating area with a sofa and chairs.

A modern kitchen with stainless steel appliances, white cabinetry, and a granite countertop.

A bedroom with a large bed, wooden beams, a nightstand, a wall-mounted light, and a door.

A single-story house with a garage, a front door, and a small front yard with bushes and a street lamp.

5. Retreat Near Boston with Roku, Deck, BBQ , Piano + Fenced in Yard for Pets!

Retreat Near Boston with Roku, Deck, BBQ , Piano + Fenced in Yard for Pets!

Framingham

10.0 out of 10, Exceptional, (3 reviews)

10/10

Exceptional

(3 reviews)

"Clean, pet friendly"

Rebecca M.

The price is ￥92,898

￥92,898

￥161,827 total

includes taxes & fees

Nov 28 - Nov 29

Retreat Near Boston with Roku, Deck, BBQ , Piano + Fenced in Yard for Pets!

A living room with a round table, two armchairs, a TV mounted on the wall, and a potted plant.

A neatly made bed with a headboard, a bedside table with a lamp, and a basket of toiletries on the bed.

A kitchen with wooden cabinets, a dishwasher, a microwave, an oven, and granite countertops.

A modern living room with a white sofa, a round coffee table, and a dining area with a white table and gold chairs. There is a large window with curtains, a potted plant, and framed artwork on the walls.

6. Beautiful two-story home close to downtown worcester 5beds-4bedroom

Beautiful two-story home close to downtown worcester 5beds-4bedroom

Worcester

9.0 out of 10, Wonderful, (20 reviews)

9.0/10

Wonderful

(20 reviews)

"Great house-clean, great location."

Kathleen R.

The price is ￥31,282

￥31,282

￥64,916 total

includes taxes & fees

Oct 31 - Nov 1

Beautiful two-story home close to downtown worcester 5beds-4bedroom

Two Adirondack chairs on a wooden deck with a view of a lake and trees.

A spacious living room with a leather sofa, a round coffee table, and a bookshelf.

A kitchen with a wooden table, bar stools, a refrigerator, a coffee machine, and a fire extinguisher.

A backyard with a wooden deck, a swing set, and a view of a lake.

7. Worcester Lakefront Cottage Apt w/ Shared Dock!

Worcester Lakefront Cottage Apt w/ Shared Dock!

Worcester

9.4 out of 10, Exceptional, (19 reviews)

9.4/10

Exceptional

(19 reviews)

"The host was very accommodating and responsive. Great property in a great location, would stay again!"

Michaela H.

The price is ￥27,806

￥27,806

￥72,509 total

includes taxes & fees

Nov 22 - Nov 23

Worcester Lakefront Cottage Apt w/ Shared Dock!

A compact, modern laundry room with a built-in washer and dryer, a small storage cabinet, and a tiled floor.

A hallway leading to a bedroom with a bed, a window with curtains, and a door marked with the number 22.

A two-story house with a central entrance, a brick foundation, and a large front yard.

A modern hallway with a black and white patterned carpet, a staircase with a granite handrail, and a door with a black frame.

8. Angel Sky Challenge

Angel Sky Challenge

Worcester

2.0 out of 10, (1 review)

2.0/10

(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 "

Cameron R.

The price is ￥25,198

￥25,198

￥41,276 total

includes taxes & fees

Nov 6 - Nov 7

Angel Sky Challenge

A spacious living area with a large sectional sofa, a glass coffee table, and a view of the outdoors through large windows.

A spacious living area with a high ceiling, wooden flooring, a large sofa, a coffee table, and a green accent wall.

A modern kitchen with wooden cabinetry, stainless steel appliances, and a hardwood floor.

A spacious living area with a fireplace, a large window, and a kitchen area with modern appliances.

9. 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, (7 reviews)

10/10

Exceptional

(7 reviews)

"Easy-to-find location and charming accommodations. Everything was organized well and very clean. Would highly recommend this listing."

Eva O.

The price is ￥28,438

￥28,438

￥41,824 total

includes taxes & fees

Nov 4 - Nov 5

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

A spacious living room with a high ceiling, a wooden floor, a black sofa, a white armchair, a small round table, and a window with curtains.

A kitchen with wooden cabinets, a black refrigerator, a microwave, and a granite countertop.

A bar area with a counter, two green chairs, a refrigerator, and a neon sign on the wall.

A bedroom with a bed, a nightstand, a lamp, a TV, and a sliding glass door to a balcony.

10. Quiet Dead-End St, PS5 Pro Lounge, 35 Min to Boston

Quiet Dead-End St, PS5 Pro Lounge, 35 Min to Boston

Worcester

8.0 out of 10, Very good, (1 review)

8.0/10

Very good

(1 review)

"The house was fine overall. There were just a few things that stood out - only 3 towels but we were 4, no baking sheet for the oven, lighting in the kitchen wasn’t great, couldn’t find the house or unit number and the lock box was hard to find. The main bed was very comfortable but the pillows were not."

Laura P.

The price is ￥29,750

￥29,750

￥38,389 total

includes taxes & fees

Oct 30 - Oct 31

Quiet Dead-End St, PS5 Pro Lounge, 35 Min to Boston

A modern living room with a large sofa, a dining area with chairs, a staircase, and a large window with a view of trees.

A two-story house with a garage, a covered porch, and a stone foundation.

A dining area with a wooden table and chairs, large windows with a view of trees, and a staircase.

11. Entire home in Sterling, Massachusetts, United States

Entire home in Sterling, Massachusetts, United States

Sterling

The price is ￥44,790

￥44,790

￥111,797 total

includes taxes & fees

Nov 2 - Nov 3

Entire home in Sterling, Massachusetts, United States

A staircase with dark wooden steps and white handrails, leading to a door at the top.

A room with a blue wall, a black leather sofa, two black chairs with gold legs, and a framed artwork.

A modern interior with a dining area, a black chair, and a wall-mounted artwork.

12. Cozy & Stylish 2-bedroom 1.5 bath townhouse in central MASS Home away from Home.

Cozy & Stylish 2-bedroom 1.5 bath townhouse in central MASS Home away from Home.

Leominster

The price is ￥34,442

￥34,442

￥42,002 total

includes taxes & fees

Nov 9 - Nov 10

Cozy & Stylish 2-bedroom 1.5 bath townhouse in central MASS Home away from Home.

A modern kitchen with white cabinets, stainless steel appliances, and a central island with bar stools.

A two-story house with a stone accent wall, a covered porch with seating, and a garage.

A spacious living room with a leather sofa, a dining table with chairs, and a kitchen in the background.

A spacious room with hardwood flooring, a dining area with a table and chairs, a fireplace, and a television.

13. 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, (3 reviews)

10/10

Exceptional

(3 reviews)

"Communication with owner was very responsive and timely. House was clean and as description. Any problems were immediately addressed by owner."

larry d.

The price is ￥51,663

￥51,663

￥80,491 total

includes taxes & fees

Nov 3 - Nov 4

4-bedroom house in nice Holden with WiFi, AC

A kitchen with a granite countertop, stainless steel sink, and dishwasher. There is a window with a view of greenery outside.

A neatly made bed with white linens and pillows, a bedside mirror, and a small potted plant on a wooden stool.

A view of a parking lot with cars, a building with a covered area, and a lake in the background.

A covered porch with two wicker chairs, a small table, and a potted plant.

14. Lakeview Getaway with Hot Tub

Lakeview Getaway with Hot Tub

Billerica

9.4 out of 10, Exceptional, (3 reviews)

9.4/10

Exceptional

(3 reviews)

"Great stay!"

KrackleJak

The price is ￥41,788

￥41,788

￥98,347 total

includes taxes & fees

Nov 1 - Nov 2

Lakeview Getaway with Hot Tub

A modern kitchen with white cabinets, a marble countertop, and pendant lighting.

A bedroom with a wooden bed, bedside lamps, a window with sheer curtains, and a bench by the window.

A hallway with a wooden door, a mirror, a small table with a notebook, and a basket with shoes.

A living room with a green sofa, two white armchairs, a coffee table with decorative items, a flat-screen TV, and a kitchen area with a refrigerator and dining table.

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

Modern Upper-Level Oasis, Minutes to Boston.

Norwood

9.8 out of 10, Exceptional, (9 reviews)

9.8/10

Exceptional

(9 reviews)

"Cute, welcoming, and everything we needed. Host was very responsive and we had a blast."

Travis B.

The price is ￥29,860

￥29,860

￥67,414 total

includes taxes & fees

Nov 2 - Nov 3

Modern Upper-Level Oasis, Minutes to Boston.

A modern kitchen with a central island, stainless steel appliances, and green bar stools.

A bedroom with a bed, a flat-screen TV, a mirror, and a wooden floor.

A stainless steel kitchen sink with a modern faucet, a soap dispenser, and a dish brush.

A modern kitchen with a central island, green chairs, a black leather sofa, and a potted plant.

16. Lake Access 4 Bed 3 Full Bath

Lake Access 4 Bed 3 Full Bath

Billerica

9.8 out of 10, Exceptional, (24 reviews)

9.8/10

Exceptional

(24 reviews)

"The house was perfect for us! Sparkling clean and comfortable. We really enjoyed staying here and would stay again for sure!"

Diane B.

The price is ￥49,964

￥49,964

￥122,376 total

includes taxes & fees

Nov 2 - Nov 3

Lake Access 4 Bed 3 Full Bath

A modern kitchen with a stainless steel refrigerator, double sink, and wooden flooring.

A red door with a white frame, two wall-mounted lights, and a welcome mat with a striped design.

A compact kitchen with a stainless steel refrigerator, a microwave, and a built-in oven. It features white cabinetry, a wooden floor, and a window providing a view of the outside.

A hallway with wooden flooring, a black console table, a staircase with white railings, and a door leading to a kitchen area.

17. Spacious 4-bedroom with four and half bathrooms

Spacious 4-bedroom with four and half bathrooms

Worcester

9.8 out of 10, Exceptional, (23 reviews)

9.8/10

Exceptional

(23 reviews)

"Great, clean location to stay."

Mike O.

The price is ￥43,310

￥43,310

￥80,391 total

includes taxes & fees

Nov 10 - Nov 11

Spacious 4-bedroom with four and half bathrooms

A modern kitchen with white cabinets, a built-in microwave, and a coffee machine.

A bedroom with a wooden ceiling, a bed with a beige quilt, a nightstand, a lamp, a TV, and a window with a view of greenery.

A dining area with a white table set for four, a potted plant, and artwork on the wall.

A modern kitchen with white cabinets, a black microwave, a coffee machine, and a toaster.

18. Newly Renovated 3BR Private Home in Newton

Newly Renovated 3BR Private Home in Newton

Newton Center

The price is ￥37,033

￥37,033

￥59,719 total

includes taxes & fees

Nov 17 - Nov 18

Newly Renovated 3BR Private Home in Newton

A cozy attic bedroom with a skylight, a piano, a mirror, and a bedside table with a lamp.

A two-story building with a garage, a balcony, and a flag.

A living room with a television, a sofa, a coffee table, a globe, and a fireplace.

A room with a wooden ceiling, a ceiling fan, a sectional sofa, a coffee table, and a patterned rug.

19. Clifford Luxury Retreat 3BR Self Check In Home

Clifford Luxury Retreat 3BR Self Check In Home

Northbridge

8.6 out of 10, Excellent, (7 reviews)

8.6/10

Excellent

(7 reviews)

The price is ￥70,871

￥70,871

￥84,566 total

includes taxes & fees

Oct 29 - Oct 30

Clifford Luxury Retreat 3BR Self Check In Home

A living room with a glass coffee table, two sofas, a dining table with chairs, and lamps.

An outdoor patio with a glass table and chairs, a red umbrella, and a white fence.

A two-story house with a porch, stone wall, and a white fence.

A bedroom with a wooden bed, two bedside tables, a ceiling fan, a window with curtains, and a patterned rug.

20. 4BR Family Vacation Home • Near Boston • Gillette Stadium • Free Parking

4BR Family Vacation Home • Near Boston • Gillette Stadium • Free Parking

Norwood

10.0 out of 10, Exceptional, (3 reviews)

10/10

Exceptional

(3 reviews)

"Not only was Joseph, our host, very accommodating, but the house was amazing! Each bed was comfortable, and each room had a TV. The life size connect 4, the video games, and the fact that every room had AC was an exciting surprise. I would definitely recommend staying here."

Chris B.

The price is ￥51,900

￥51,900

￥115,150 total

includes taxes & fees

Oct 29 - Oct 30

4BR Family Vacation Home • Near Boston • Gillette Stadium • Free Parking

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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