
Upton Vacation Rentals
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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 HomeNorthbridge
8.6 out of 10, Excellent, (7 reviews)
The price is CA $547
CA $623 total
includes taxes & fees
Nov 9 - Nov 10

2. Quiet Dead-End St, PS5 Pro Lounge, 35 Min to Boston
Quiet Dead-End St, PS5 Pro Lounge, 35 Min to BostonWorcester
8.0 out of 10, Very good, (1 review)
The price is CA $361
CA $449 total
includes taxes & fees
Nov 11 - Nov 12

3. Angel Sky Challenge
Angel Sky ChallengeWorcester
2.0 out of 10, (1 review)
The price is CA $226
CA $335 total
includes taxes & fees
Nov 9 - Nov 10

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 price is CA $249
CA $623 total
includes taxes & fees
Nov 22 - Nov 23

5. Wizard's Roost at Underhill Hollow
Wizard's Roost at Underhill HollowNorth Grosvenordale
9.6 out of 10, Exceptional, (26 reviews)
The price is CA $178
CA $256 total
includes taxes & fees
Nov 10 - Nov 11

6. The Tree House at Underhill Hollow
The Tree House at Underhill HollowThompson
9.4 out of 10, Exceptional, (46 reviews)
The price is CA $178
CA $254 total
includes taxes & fees
Nov 9 - Nov 10

7. SteamPunk Bunk House and Intergalactic Way Station
SteamPunk Bunk House and Intergalactic Way StationThompson
10.0 out of 10, Exceptional, (20 reviews)
The price is CA $178
CA $246 total
includes taxes & fees
Nov 9 - Nov 10

8. Spacious 4-bedroom with four and half bathrooms
Spacious 4-bedroom with four and half bathroomsWorcester
9.8 out of 10, Exceptional, (23 reviews)
The price is CA $389
CA $661 total
includes taxes & fees
Nov 9 - Nov 10

9. totally remodeled house with fitness room, close to Boston and Worcester
totally remodeled house with fitness room, close to Boston and WorcesterFramingham
9.0 out of 10, Wonderful, (18 reviews)
The price is CA $266
CA $459 total
includes taxes & fees
Nov 12 - Nov 13

10. Spacious 5 Bedroom Retreat • Free Parking • Pet Friendly• Greater Boston
Spacious 5 Bedroom Retreat • Free Parking • Pet Friendly• Greater BostonFramingham
10.0 out of 10, Exceptional, (5 reviews)
The price is CA $493
CA $804 total
includes taxes & fees
Nov 11 - Nov 12

11. 4-bedroom house in nice Holden with WiFi, AC
4-bedroom house in nice Holden with WiFi, ACHolden
10.0 out of 10, Exceptional, (3 reviews)
The price is CA $671
CA $924 total
includes taxes & fees
Nov 22 - Nov 23

12. Newly Renovated beautiful 3-Bed 2-Bath Home with Easy Airport Access
Newly Renovated beautiful 3-Bed 2-Bath Home with Easy Airport AccessFramingham
9.6 out of 10, Exceptional, (35 reviews)
The price is CA $322
CA $519 total
includes taxes & fees
Nov 30 - Dec 1

13. Cottage by the Castle – Downtown Spencer
Cottage by the Castle – Downtown SpencerSpencer
10.0 out of 10, Exceptional, (9 reviews)
The price is CA $291
CA $318 total
includes taxes & fees
Nov 9 - Nov 10

14. Luxury Boston Ranch –Sleeps 8|Pet+|Heated pool
Luxury Boston Ranch –Sleeps 8|Pet+|Heated poolFramingham
10.0 out of 10, Exceptional, (6 reviews)
The price is CA $471
CA $878 total
includes taxes & fees
Nov 23 - Nov 24

15. Welcome in this charming one bedroom apartment located in Westwood. WorldCup2026
Welcome in this charming one bedroom apartment located in Westwood. WorldCup2026Westwood
10.0 out of 10, Exceptional, (8 reviews)
The price is CA $318
CA $437 total
includes taxes & fees
Nov 15 - Nov 16

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)
The price is CA $525
CA $1,063 total
includes taxes & fees
Nov 23 - Nov 24

17. Luxury Home - Fire Pit - Beach Grill - 2 Decks
Luxury Home - Fire Pit - Beach Grill - 2 DecksSmithfield
10.0 out of 10, Exceptional, (21 reviews)
The price is CA $335
CA $895 total
includes taxes & fees
Nov 9 - Nov 10

18. 4BR Family Vacation Home • Near Boston • Gillette Stadium • Free Parking
4BR Family Vacation Home • Near Boston • Gillette Stadium • Free ParkingNorwood
10.0 out of 10, Exceptional, (3 reviews)
The price is CA $464
CA $989 total
includes taxes & fees
Nov 20 - Nov 21

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

20. Modern Upper-Level Oasis, Minutes to Boston.
Modern Upper-Level Oasis, Minutes to Boston.Norwood
9.8 out of 10, Exceptional, (9 reviews)
The price is CA $254
CA $532 total
includes taxes & fees
Nov 9 - Nov 10
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

DoubleTree by Hilton Hotel Boston - Westborough
10/10 Excellent
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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