A town with a prominent church, a large building with a clock tower, and a mix of residential and commercial buildings surrounded by greenery.

Villas in Winchester

Check prices for these dates

In two weeks
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21
No exact matches found, but these alternatives could be just right

Recommended hotels in Winchester

A residential street with houses, a car parked on the side, and a tree with autumn leaves.

1. Train to Boston! Cozy Apartment in Winchester

Train to Boston! Cozy Apartment in Winchester
3.0 star property
Winchester
10.0 out of 10, Exceptional, (1 review)
"Clean and spacious private entrance mother-in-law suite in a nice and quiet neighborhood. About a 25-40 minute ride, depending on traffic, into Boston."
United States
Selena
$241 nightly
The price is $270
Nov 17 - Nov 18
Total with taxes and fees
Train to Boston! Cozy Apartment in Winchester
A modern hotel entrance with a covered walkway, a glass facade, and a landscaped area with shrubs and trees.

2. Best Western Plus New Englander

Best Western Plus New Englander
2.5 star property
Woburn
8.6 out of 10, Excellent, (1,163 reviews)
"Perfect location to get around the area and a nice hotel"
United States
Madison
$105 nightly
The price is $117
Nov 15 - Nov 16
Total with taxes and fees
Best Western Plus New Englander
A Hampton Inn hotel with a modern design, featuring a central entrance and multiple floors.

3. Hampton Inn Boston Bedford Burlington

Hampton Inn Boston Bedford Burlington
2.5 star property
Billerica
9.2 out of 10, Wonderful, (1,004 reviews)
"The breakfast was delicious."
Canada
François
$97 nightly
The price is $108
Nov 20 - Nov 21
Total with taxes and fees
Hampton Inn Boston Bedford Burlington
A multi-story hotel with a brick facade and a sign for 'Sonesta Simply Suites'.

4. Sonesta Simply Suites Boston Burlington

Sonesta Simply Suites Boston Burlington
2.0 star property
Burlington
8.8 out of 10, Excellent, (552 reviews)
"Clean room, staff was wonderful"
United States
Cara A
$89 nightly
The price is $99
Nov 15 - Nov 16
Total with taxes and fees
Sonesta Simply Suites Boston Burlington
An outdoor patio area with tables and chairs, a fire feature, and a view of the street.

5. Archer Hotel Boston/Burlington

Archer Hotel Boston/Burlington
4.0 star property
Burlington
9.8 out of 10, Exceptional, (1,005 reviews)
"The location is excellent."
United States
Dong Jin
$141 nightly
The price is $158
Nov 23 - Nov 24
Total with taxes and fees
Archer Hotel Boston/Burlington
A modern lobby with a leather sofa, two round wooden tables, a flat-screen TV mounted on a textured wall, and a glass partition with a view of the outdoors.

6. Four Points by Sheraton Boston Newton

Four Points by Sheraton Boston Newton
3.5 star property
Newton Corner
8.4 out of 10, Very good, (2,695 reviews)
"Great place to stay for our weekend in Boston!"
United States
Ellen
$93 nightly
The price is $103
Nov 22 - Nov 23
Total with taxes and fees
Four Points by Sheraton Boston Newton
An outdoor patio with stone walls, a pool table, and seating areas.

7. Comfort Inn & Suites Logan International Airport

Comfort Inn & Suites Logan International Airport
2.5 star property
Revere
9.0 out of 10, Wonderful, (2,440 reviews)
"Super clean and the airport shuttle was excellent."
United States
Albert R Kaupp
$118 nightly
The price is $131
Nov 26 - Nov 27
Total with taxes and fees
Comfort Inn & Suites Logan International Airport
An outdoor wedding ceremony setup with a white aisle, chairs, and floral decorations.

8. Lakeside Inn

Lakeside Inn
2.0 star property
Wakefield
8.2 out of 10, Very good, (1,069 reviews)
"Good place to stay"
United States
Robert
$94 nightly
The price is $105
Nov 26 - Nov 27
Total with taxes and fees
Lakeside Inn
A modern hotel with a prominent 'Hyatt House' sign, featuring a symmetrical facade, large windows, and a landscaped entrance area.

9. HYATT house Boston/Waltham

HYATT house Boston/Waltham
3.0 star property
Waltham
9.0 out of 10, Wonderful, (1,173 reviews)
"I always enjoy staying at this hotel whenever I visit Boston."
United States
Dongho
$122 nightly
The price is $136
Nov 20 - Nov 21
Total with taxes and fees
HYATT house Boston/Waltham
A Hampton Inn hotel with a modern brick facade, large windows, and a parking lot.

10. Hampton Inn Boston Logan Airport Chelsea

Hampton Inn Boston Logan Airport Chelsea
2.5 star property
Chelsea
9.0 out of 10, Wonderful, (3,289 reviews)
"I enjoyed staying here"
United States
Velma
$110 nightly
The price is $122
Nov 23 - Nov 24
Total with taxes and fees
Hampton Inn Boston Logan Airport Chelsea
A modern building with a prominent 'CAMBRIA' sign, featuring a multi-story structure with large windows and a flat roof.

11. Cambria Hotel Boston Somerville

Cambria Hotel Boston Somerville
3.0 star property
Spring Hill
9.8 out of 10, Exceptional, (1,002 reviews)
"Fantastic hotel and great location!"
United States
Mary
$135 nightly
The price is $151
Nov 23 - Nov 24
Total with taxes and fees
Cambria Hotel Boston Somerville
A modern building with a courtyard, benches, and flower beds.

12. Porter Square Hotel

Porter Square Hotel
3.0 star property
North Cambridge
9.2 out of 10, Wonderful, (1,006 reviews)
"Great place to stay!"
United States
Gerardo
$135 nightly
The price is $157
Nov 22 - Nov 23
Total with taxes and fees
Porter Square Hotel
A Hampton Inn hotel with a parking lot and a covered entrance.

13. Hampton Inn Boston - Logan Airport

Hampton Inn Boston - Logan Airport
3.0 star property
Revere
8.2 out of 10, Very good, (5,531 reviews)
"Nice little Cafe and the rooms were well equipped"
United States
Bruce
$98 nightly
The price is $109
Nov 25 - Nov 26
Total with taxes and fees
Hampton Inn Boston - Logan Airport
A hotel entrance with a covered walkway, large windows, and a sign indicating Staybridge Suites.

14. Holiday Inn Express Boston Logan Airport - Revere by IHG

Holiday Inn Express Boston Logan Airport - Revere by IHG
2.5 star property
Revere
9.2 out of 10, Wonderful, (1,452 reviews)
"Great location near the airport"
United States
Regina
$95 nightly
The price is $106
Nov 25 - Nov 26
Total with taxes and fees
Holiday Inn Express Boston Logan Airport - Revere by IHG
A modern building with a curved glass facade and a central entrance.

15. The Westin Waltham-Boston

The Westin Waltham-Boston
4.0 star property
Waltham
9.0 out of 10, Wonderful, (1,141 reviews)
"The room was so clean and beautiful and smelled good and the staff was really friendly and the parking was across from the hotel and the hotel was just fancy"
United States
Karen
$108 nightly
The price is $121
Nov 23 - Nov 24
Total with taxes and fees
The Westin Waltham-Boston
A hotel with a modern facade, a parking lot, and two parked cars.

16. enVision Hotel Boston Everett

enVision Hotel Boston Everett
2.0 star property
Everett
8.4 out of 10, Very good, (1,017 reviews)
"Great place way cheaper than downtown Boston!"
United States
Scott
$119 nightly
The price is $133
Nov 24 - Nov 25
Total with taxes and fees
enVision Hotel Boston Everett
A modern hotel with a prominent 'Avid' sign, large windows, and a well-lit entrance.

17. avid hotel Boston Logan Airport - Revere by IHG

avid hotel Boston Logan Airport - Revere by IHG
2.5 star property
Revere
9.0 out of 10, Wonderful, (1,717 reviews)
"Reasonable price, clean, comfy beds—would stay there again!"
United States
Steve
$107 nightly
The price is $120
Nov 26 - Nov 27
Total with taxes and fees
avid hotel Boston Logan Airport - Revere by IHG
A multi-story building with a sign reading "Embassy Suites."

18. Embassy Suites by Hilton Boston Waltham

Embassy Suites by Hilton Boston Waltham
3.5 star property
Waltham
8.2 out of 10, Very good, (3,101 reviews)
"Great place to stay"
United States
Wesly
$106 nightly
The price is $118
Nov 23 - Nov 24
Total with taxes and fees
Embassy Suites by Hilton Boston Waltham
A multi-story hotel with balconies, a restaurant on the ground floor, and a stone facade.

19. Best Western Plus Waltham Boston

Best Western Plus Waltham Boston
3.0 star property
Piety Corner
8.4 out of 10, Very good, (1,355 reviews)
"Friendly staff very clean hotel"
United States
carrie
$106 nightly
The price is $118
Nov 24 - Nov 25
Total with taxes and fees
Best Western Plus Waltham Boston
A multi-story hotel with a modern design, featuring a prominent 'Hampton Inn' sign, a 'Buffalo Wild Wings' restaurant, and a 'Premier Dental' clinic.

20. Hampton Inn & Suites Watertown Boston

Hampton Inn & Suites Watertown Boston
2.5 star property
Watertown
9.2 out of 10, Wonderful, (1,220 reviews)
"Would stay again!"
United States
Emma
$118 nightly
The price is $132
Nov 22 - Nov 23
Total with taxes and fees
Hampton Inn & Suites Watertown 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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winchester Hotel Reviews

Four Points by Sheraton Boston Newton

Four Points by Sheraton Boston Newton

8/10 Good
"I"
Patricia 3-night trip
Posted 1 hour ago
Four Points by Sheraton Boston Newton

Find out more about Winchester

Winchester Villas information

Number of reviews
12,946
Accommodation
4 Villas
Lowest Price
$99
Highest Price
$270

Explore a world of travel with Expedia