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Our top choices for Upton vacation homes

1. 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)
"We loved our stay here. The home and the host were both exceptional. We highly recommend this home!"
United States
Martin G.
The price is CA $547
CA $623 total
includes taxes & fees
Nov 9 - Nov 10
Clifford Luxury Retreat 3BR Self Check In Home

2. 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)
"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."
United States
Laura P.
The price is CA $361
CA $449 total
includes taxes & fees
Nov 11 - Nov 12
Quiet Dead-End St, PS5 Pro Lounge, 35 Min to Boston

3. 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 CA $226
CA $335 total
includes taxes & fees
Nov 9 - Nov 10
Angel Sky Challenge

4. Worcester Lakefront Cottage Apt w/ Shared Dock!

Worcester Lakefront Cottage Apt w/ Shared Dock!
Worcester
9.4 out of 10, Exceptional, (19 reviews)
"The host was very accommodating and responsive. Great property in a great location, would stay again!"
United States
Michaela H.
The price is CA $249
CA $623 total
includes taxes & fees
Nov 22 - Nov 23
Worcester Lakefront Cottage Apt w/ Shared Dock!

5. Wizard's Roost at Underhill Hollow

Wizard's Roost at Underhill Hollow
North Grosvenordale
9.6 out of 10, Exceptional, (26 reviews)
"Great stay!!"
United States
Elizabeth G.
The price is CA $178
CA $256 total
includes taxes & fees
Nov 10 - Nov 11
Wizard's Roost at Underhill Hollow

6. The Tree House at Underhill Hollow

The Tree House at Underhill Hollow
Thompson
9.4 out of 10, Exceptional, (46 reviews)
"Nice place to stay has good air conditioning "
United States
Zachary P.
The price is CA $178
CA $254 total
includes taxes & fees
Nov 9 - Nov 10
The Tree House at Underhill Hollow

7. SteamPunk Bunk House and Intergalactic Way Station

SteamPunk Bunk House and Intergalactic Way Station
Thompson
10.0 out of 10, Exceptional, (20 reviews)
"Enjoyed our stay. Loved being out in the countryside "
United States
Pauline S.
The price is CA $178
CA $246 total
includes taxes & fees
Nov 9 - Nov 10
SteamPunk Bunk House and Intergalactic Way Station

8. 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)
"Great, clean location to stay."
United States
Mike O.
The price is CA $389
CA $661 total
includes taxes & fees
Nov 9 - Nov 10
Spacious 4-bedroom with four and half bathrooms

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

totally remodeled house with fitness room, close to Boston and Worcester
Framingham
9.0 out of 10, Wonderful, (18 reviews)
"The property was just what we wanted and worked very well for our family of six."
United States
Levi O.
The price is CA $266
CA $459 total
includes taxes & fees
Nov 12 - Nov 13
totally remodeled house with fitness room, close to Boston and Worcester

10. 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 CA $493
CA $804 total
includes taxes & fees
Nov 11 - Nov 12
Spacious 5 Bedroom Retreat • Free Parking • Pet Friendly• Greater Boston

11. 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)
"Communication with owner was very responsive and timely. House was clean and as description. Any problems were immediately addressed by owner."
United States
larry d.
The price is CA $671
CA $924 total
includes taxes & fees
Nov 22 - Nov 23
4-bedroom house in nice Holden with WiFi, AC

12. 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)
"We had a great stay."
United States
Jessica D.
The price is CA $322
CA $519 total
includes taxes & fees
Nov 30 - Dec 1
Newly Renovated beautiful 3-Bed 2-Bath Home with Easy Airport Access

13. Cottage by the Castle – Downtown Spencer

Cottage by the Castle – Downtown Spencer
Spencer
10.0 out of 10, Exceptional, (9 reviews)
"Nice, clean and well maintained. Would stay here again."
United States
Sarah S.
The price is CA $291
CA $318 total
includes taxes & fees
Nov 9 - Nov 10
Cottage by the Castle – Downtown Spencer

14. 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 CA $471
CA $878 total
includes taxes & fees
Nov 23 - Nov 24
Luxury Boston Ranch –Sleeps 8|Pet+|Heated pool

15. 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, (8 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 CA $318
CA $437 total
includes taxes & fees
Nov 15 - Nov 16
Welcome in this charming one bedroom apartment located in Westwood. WorldCup2026

16. 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)
"Clean, pet friendly"
United States
Rebecca M.
The price is CA $525
CA $1,063 total
includes taxes & fees
Nov 23 - Nov 24
Retreat Near Boston with Roku, Deck, BBQ , Piano + Fenced in Yard for Pets!

17. Luxury Home - Fire Pit - Beach Grill - 2 Decks

Luxury Home - Fire Pit - Beach Grill - 2 Decks
Smithfield
10.0 out of 10, Exceptional, (21 reviews)
"Has everything you need to feel at home great place"
United States
Jason R.
The price is CA $335
CA $895 total
includes taxes & fees
Nov 9 - Nov 10
Luxury Home - Fire Pit - Beach Grill - 2 Decks

18. 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)
"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."
United States
Chris B.
The price is CA $464
CA $989 total
includes taxes & fees
Nov 20 - Nov 21
4BR Family Vacation Home • Near Boston • Gillette Stadium • Free Parking

19. Entire home in Sterling, Massachusetts, United States

Entire home in Sterling, Massachusetts, United States
Sterling
The price is CA $445
CA $1,021 total
includes taxes & fees
Nov 10 - Nov 11
Entire home in Sterling, Massachusetts, United States

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

Modern Upper-Level Oasis, Minutes to Boston.
Norwood
9.8 out of 10, Exceptional, (9 reviews)
"Cute, welcoming, and everything we needed. Host was very responsive and we had a blast."
United States
Travis B.
The price is CA $254
CA $532 total
includes taxes & fees
Nov 9 - Nov 10
Modern Upper-Level Oasis, Minutes to Boston.
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 Upton Hotel Reviews

Find out more about Upton

Upton Vacation Homes information

Number of reviews
245
Accommodation
153 Vacation Homes
Lowest Price
CA $246
Highest Price
CA $1,063

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