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Our top choices for Winchester holiday rentals

1. Crescent Suites Hotel
Crescent Suites HotelSouth Side
9.6 out of 10, Exceptional, (1,345 reviews)
The price is £126
includes taxes & fees
8 Nov - 9 Nov

2. Charming 1-bedroom well located Garden Apartment in Historic West Medford
Charming 1-bedroom well located Garden Apartment in Historic West MedfordWest Medford
10.0 out of 10, Exceptional, (18 reviews)
The price is £192
includes taxes & fees
15 Nov - 16 Nov

3. Marriott Vacation Club® at Custom House, Boston
Marriott Vacation Club® at Custom House, BostonDowntown Boston
9.4 out of 10, Exceptional, (680 reviews)
The price is £195
includes taxes & fees
25 Nov - 26 Nov

4. Enchanting Hidden Door Escape
Enchanting Hidden Door EscapeStoneham
9.6 out of 10, Exceptional, (37 reviews)
The price is £449
includes taxes & fees
15 Nov - 16 Nov

5. Near Boston Historic two-bedroom with Modern Amenities
Near Boston Historic two-bedroom with Modern AmenitiesMalden
10.0 out of 10, Exceptional, (338 reviews)
The price is £212
includes taxes & fees
8 Nov - 9 Nov

6. 5-bedroom house. Close to airport, bus & train. 10 min from Boston. Sleeps 10.
5-bedroom house. Close to airport, bus & train. 10 min from Boston. Sleeps 10.Melrose
10.0 out of 10, Exceptional, (156 reviews)
The price is £412
includes taxes & fees
17 Nov - 18 Nov

7. Global Luxury Suites Downtown Boston
Global Luxury Suites Downtown BostonChinatown
8.0 out of 10, Very good, (772 reviews)
The price is £177
includes taxes & fees
7 Dec - 8 Dec

8. Kasa Boston at Fenway
Kasa Boston at FenwayFenway–Kenmore
8.8 out of 10, Excellent, (348 reviews)
The price is £220
includes taxes & fees
10 Nov - 11 Nov

9. Boston 2bd King Bed near Harvard, MIT, subway near Boston. On-site free Parking
Boston 2bd King Bed near Harvard, MIT, subway near Boston. On-site free ParkingWard Two
10.0 out of 10, Exceptional, (25 reviews)
The price is £270
includes taxes & fees
8 Nov - 9 Nov

10. The Chester Hotel
The Chester HotelSouth End
8.8 out of 10, Excellent, (43 reviews)
The price is £217
includes taxes & fees
22 Nov - 23 Nov

11. Maverick Suites at 28 Fenway
Maverick Suites at 28 FenwayFenway–Kenmore
8.6 out of 10, Excellent, (473 reviews)
The price is £160
includes taxes & fees
1 Dec - 2 Dec

12. Maverick Suites at 89 Marion
Maverick Suites at 89 MarionCoolidge Corner
8.4 out of 10, Very good, (355 reviews)
The price is £151
includes taxes & fees
1 Dec - 2 Dec

13. Global Luxury Suites East Boston
Global Luxury Suites East BostonEast Boston
6.8 out of 10, (215 reviews)
The price is £192
includes taxes & fees
29 Nov - 30 Nov

14. Spacious Modern Luxury Duplex Near Boston & Cambridge - Free Parking
Spacious Modern Luxury Duplex Near Boston & Cambridge - Free ParkingEverett
10.0 out of 10, Exceptional, (37 reviews)
The price is £283
includes taxes & fees
11 Nov - 12 Nov

15. Maverick Suites at 245 Newbury St
Maverick Suites at 245 Newbury StBack Bay
8.4 out of 10, Very good, (219 reviews)
The price is £153
includes taxes & fees
6 Dec - 7 Dec

16. Charlesgate Suites
Charlesgate SuitesFenway–Kenmore
9.2 out of 10, Wonderful, (246 reviews)
The price is £275
includes taxes & fees
23 Nov - 24 Nov

17. The Concord Hotel
The Concord HotelSouth End
8.0 out of 10, Very good, (38 reviews)
The price is £230
includes taxes & fees
8 Nov - 9 Nov

18. 3BR2Bth TD Garden/MIT/Harvard/BOS/3 Parking Spaces
3BR2Bth TD Garden/MIT/Harvard/BOS/3 Parking SpacesEast Somerville
10.0 out of 10, Exceptional, (31 reviews)
The price is £291
includes taxes & fees
8 Nov - 9 Nov

19. Maverick Suites at 40 Temple St
Maverick Suites at 40 Temple StBeacon Hill
8.0 out of 10, Very good, (165 reviews)
The price is £154
includes taxes & fees
9 Nov - 10 Nov

20. Charming 2-bedroom condo in delightful Chelsea with WiFi, AC
Charming 2-bedroom condo in delightful Chelsea with WiFi, ACChelsea
8.6 out of 10, Excellent, (10 reviews)
The price is £270
includes taxes & fees
9 Nov - 10 Nov
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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