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

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31
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
Oct 8 - Oct 9
Total with taxes and fees
Train to Boston! Cozy Apartment in Winchester
A residential street with houses, a car parked on the side, and a tree with autumn leaves.

2. Train to Boston! Cozy Apartment in Winchester

Train to Boston! Cozy Apartment in Winchester
Winchester
10.0 out of 10, Exceptional, (3 reviews)
"Nice Appartement!Bus round the corner, very quiet!"
United States
Holger V.
$245 nightly
The price is $274
Oct 8 - Oct 9
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.

3. Best Western Plus New Englander

Best Western Plus New Englander
2.5 star property
Woburn
8.6 out of 10, Excellent, (1,146 reviews)
"Perfect location to get around the area and a nice hotel"
United States
Madison
$114 nightly
The price is $127
Nov 1 - Nov 2
Total with taxes and fees
Best Western Plus New Englander
A modern hotel with a covered entrance, multiple floors, and a landscaped area in front.

4. Hampton Inn Boston Woburn

Hampton Inn Boston Woburn
2.5 star property
Woburn
9.0 out of 10, Wonderful, (1,523 reviews)
"It was a good and clean hotel."
United States
Pamela
$139 nightly
The price is $155
Nov 1 - Nov 2
Total with taxes and fees
Hampton Inn Boston Woburn
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, (1,001 reviews)
"Super cute hotel!"
United States
Angelina
$161 nightly
The price is $180
Nov 7 - Nov 8
Total with taxes and fees
Archer Hotel Boston/Burlington
A multi-story hotel with a brick facade and a sign for 'Sonesta Simply Suites'.

6. Sonesta Simply Suites Boston Burlington

Sonesta Simply Suites Boston Burlington
2.0 star property
Burlington
8.8 out of 10, Excellent, (509 reviews)
"Great place, very clean, staff was helpful"
United States
Jeffrey
$103 nightly
The price is $115
Nov 6 - Nov 7
Total with taxes and fees
Sonesta Simply Suites 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.

7. 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, (2,690 reviews)
"Was a great stay."
United States
Samantha
$114 nightly
The price is $127
Nov 1 - Nov 2
Total with taxes and fees
Four Points by Sheraton Boston Newton
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, (967 reviews)
"Good place to stay"
United States
Robert
$144 nightly
The price is $161
Nov 1 - Nov 2
Total with taxes and fees
Lakeside Inn
A Hampton Inn hotel with a modern design, featuring a central entrance and multiple floors.

9. Hampton Inn Boston Bedford Burlington

Hampton Inn Boston Bedford Burlington
2.5 star property
Billerica
9.2 out of 10, Wonderful, (1,005 reviews)
"The breakfast was delicious."
Canada
François
$94 nightly
The price is $104
Nov 6 - Nov 7
Total with taxes and fees
Hampton Inn Boston Bedford Burlington
A modern building with a curved glass facade and a central entrance.

10. The Westin Waltham-Boston

The Westin Waltham-Boston
4.0 star property
Waltham
9.0 out of 10, Wonderful, (1,125 reviews)
"Friendly and respectful staff. Also the breakfast was delicious."
United States
Maria
$149 nightly
The price is $166
Nov 7 - Nov 8
Total with taxes and fees
The Westin 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.

11. Hampton Inn & Suites Watertown Boston

Hampton Inn & Suites Watertown Boston
2.5 star property
Watertown
9.2 out of 10, Wonderful, (1,198 reviews)
"My second stay here - convenient and nice area to eat and shop. Hotel was clean and quiet - staff friendly"
United States
Gina
$161 nightly
The price is $179
Nov 1 - Nov 2
Total with taxes and fees
Hampton Inn & Suites Watertown Boston
A hotel with a modern facade, a parking lot, and two parked cars.

12. enVision Hotel Boston Everett

enVision Hotel Boston Everett
2.0 star property
Everett
8.6 out of 10, Excellent, (1,000 reviews)
"Nice hotel, comfy beds, clean room and nice staff. Great location close to airport rental car return."
United States
Angela
$149 nightly
The price is $166
Nov 3 - Nov 4
Total with taxes and fees
enVision Hotel Boston Everett
A multi-story hotel with balconies, a restaurant on the ground floor, and a stone facade.

13. Best Western Plus Waltham Boston

Best Western Plus Waltham Boston
3.0 star property
Piety Corner
8.4 out of 10, Very good, (1,341 reviews)
"Easy to get to from the highway, great staff, wonderful breakfast."
United States
Hope
$115 nightly
The price is $128
Nov 5 - Nov 6
Total with taxes and fees
Best Western Plus Waltham Boston
A multi-story building with a sign reading "Embassy Suites."

14. Embassy Suites by Hilton Boston Waltham

Embassy Suites by Hilton Boston Waltham
3.5 star property
Waltham
8.2 out of 10, Very good, (3,054 reviews)
"Great place to stay"
United States
Wesly
$122 nightly
The price is $136
Nov 5 - Nov 6
Total with taxes and fees
Embassy Suites by Hilton Boston Waltham
A modern building with a prominent 'CAMBRIA' sign, featuring a multi-story structure with large windows and a flat roof.

15. Cambria Hotel Boston Somerville

Cambria Hotel Boston Somerville
3.0 star property
Spring Hill
9.8 out of 10, Exceptional, (1,006 reviews)
"Fantastic hotel and great location!"
United States
Mary
$199 nightly
The price is $223
Nov 1 - Nov 2
Total with taxes and fees
Cambria Hotel Boston Somerville
A modern hotel with a prominent 'Hyatt House' sign, featuring a symmetrical facade, large windows, and a landscaped entrance area.

16. HYATT house Boston/Waltham

HYATT house Boston/Waltham
3.0 star property
Waltham
9.0 out of 10, Wonderful, (1,152 reviews)
"Always a wonderful stay"
United States
Sarah
$125 nightly
The price is $140
Nov 5 - Nov 6
Total with taxes and fees
HYATT house Boston/Waltham
A modern building with a courtyard, benches, and flower beds.

17. Porter Square Hotel

Porter Square Hotel
3.0 star property
North Cambridge
9.2 out of 10, Wonderful, (1,000 reviews)
"Great place to stay!"
United States
Gerardo
$193 nightly
The price is $224
Nov 1 - Nov 2
Total with taxes and fees
Porter Square Hotel
A Hilton Garden Inn with a symmetrical facade, large entrance, and a covered walkway.

18. Hilton Garden Inn Boston/Waltham

Hilton Garden Inn Boston/Waltham
3.5 star property
Waltham
9.0 out of 10, Wonderful, (1,001 reviews)
"Nice place to stay"
United States
iram
$135 nightly
The price is $151
Nov 1 - Nov 2
Total with taxes and fees
Hilton Garden Inn Boston/Waltham
A Hampton Inn hotel with a parking lot and a covered entrance.

19. Hampton Inn Boston - Logan Airport

Hampton Inn Boston - Logan Airport
3.0 star property
Revere
8.2 out of 10, Very good, (5,533 reviews)
"I would stay here again without hesitation."
United States
Robert
$155 nightly
The price is $173
Nov 2 - Nov 3
Total with taxes and fees
Hampton Inn Boston - Logan Airport
A hotel with a large glass facade, a visible entrance, and a mailbox on the sidewalk.

20. Hotel 1868

Hotel 1868
3.5 star property
Agassiz
9.6 out of 10, Exceptional, (1,000 reviews)
"Great stay. Excellent location."
United States
peter
$231 nightly
The price is $268
Oct 31 - Nov 1
Total with taxes and fees
Hotel 1868
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 Winchester Hotel Reviews

Encore Boston Harbor

Encore Boston Harbor

10/10 Excellent
"Resort was very clean and well maintained. Parking was close and easily accessible.Room was spacious and well decorated with modern amenities and the large window gave a great view of the city. Power curtains, Alexa operated lights and TV, a tablet to conveniently control the room. Staff was attentive and helpful. The Casino had numerous table games, sports betting and slot machines. We are from out of state but would not hesitate to return if in the area."
David 2-night trip
Posted 12 hours ago
Encore Boston Harbor

Find out more about Winchester

Winchester Cottages information

Number of reviews
19,606
Accommodation
32 Cottages
Lowest Price
$104
Highest Price
$274

Frequently asked questions

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What is there to do in Winchester near my cottage?
The most useful travel accessory is a well-thought-out travel plan. Winter Pond is a wonderful spot to kick-start your sightseeing in Winchester.

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