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 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Winchester houseboats

A modern hotel entrance with a covered walkway, a glass facade, and a landscaped area with shrubs and trees.

1. Best Western Plus New Englander

Best Western Plus New Englander
2.5 star property
Woburn
8.6 out of 10, Excellent, (1,131 reviews)
"Everything was clean and had a good stay."
United States
Richard
The price is CA $197
CA $220 total
includes taxes & fees
Sep 27 - Sep 28
Best Western Plus New Englander
A modern hotel with a covered entrance, multiple floors, and a landscaped area in front.

2. Hampton Inn Boston Woburn

Hampton Inn Boston Woburn
2.5 star property
Woburn
9.0 out of 10, Wonderful, (1,511 reviews)
"The room was clean, had all the amenities you may need, served a very nice breakfast , had good parking, and near some great places to eat."
United States
Pamela
The price is CA $202
CA $225 total
includes taxes & fees
Oct 4 - Oct 5
Hampton Inn Boston Woburn
A modern lounge area with a glass wall, a central fire feature, and seating arrangements.

3. Hilton Boston/Woburn

Hilton Boston/Woburn
3.5 star property
Woburn
8.6 out of 10, Excellent, (1,476 reviews)
"Nice stay"
United States
Shawna
The price is CA $230
CA $256 total
includes taxes & fees
Oct 4 - Oct 5
Hilton Boston/Woburn
A Holiday Inn Express building with a modern facade, large windows, and a clear entrance area.

4. Holiday Inn Express Boston North-Woburn by IHG

Holiday Inn Express Boston North-Woburn by IHG
2.5 star property
Woburn
8.2 out of 10, Very good, (1,019 reviews)
"Everything was good, would definitely stay here again."
United States
Greg
The price is CA $192
CA $215 total
includes taxes & fees
Sep 27 - Sep 28
Holiday Inn Express Boston North-Woburn by IHG
A hotel entrance with a glass door, illuminated pillars, and a paved walkway.

5. Crowne Plaza Boston - Woburn by IHG

Crowne Plaza Boston - Woburn by IHG
4.0 star property
Woburn
8.6 out of 10, Excellent, (1,104 reviews)
"Great location, good breakfast."
United States
Brendan C
The price is CA $235
CA $262 total
includes taxes & fees
Oct 4 - Oct 5
Crowne Plaza Boston - Woburn by IHG
A hotel with a swimming pool, parking lot, and a view of a lake.

6. Lakeside Inn

Lakeside Inn
2.0 star property
Wakefield
8.2 out of 10, Very good, (886 reviews)
"Clean rooms, friendly staff, great breakfast."
United States
Ryan
The price is CA $173
CA $193 total
includes taxes & fees
Sep 27 - Sep 28
Lakeside Inn
A multi-story hotel with a modern architectural design, featuring large windows and a brick facade.

7. Archer Hotel Boston/Burlington

Archer Hotel Boston/Burlington
4.0 star property
Burlington
9.8 out of 10, Exceptional, (1,000 reviews)
"For the price it was a nice place to stay"
United States
Ryan
The price is CA $274
CA $306 total
includes taxes & fees
Sep 27 - Sep 28
Archer Hotel Boston/Burlington
A multi-story hotel with balconies, a restaurant on the ground floor, and a stone facade.

8. Best Western Plus Waltham Boston

Best Western Plus Waltham Boston
3.0 star property
Piety Corner
8.4 out of 10, Very good, (1,331 reviews)
"Good place to stay."
United States
Suellen
The price is CA $172
CA $193 total
includes taxes & fees
Sep 27 - Sep 28
Best Western Plus Waltham Boston
A multi-story hotel with a brick facade, multiple windows, and a visible entrance.

9. Residence Inn by Marriott Boston Burlington

Residence Inn by Marriott Boston Burlington
3.0 star property
Burlington
9.2 out of 10, Wonderful, (1,000 reviews)
"Very nice place definitely be back"
United States
Sarah
The price is CA $309
CA $346 total
includes taxes & fees
Oct 11 - Oct 12
Residence Inn by Marriott Boston Burlington
A Hampton Inn hotel with a modern design, featuring a central entrance and multiple floors.

10. Hampton Inn Boston Bedford Burlington

Hampton Inn Boston Bedford Burlington
2.5 star property
Billerica
9.2 out of 10, Wonderful, (1,003 reviews)
"Very clean room, spacious and the breakfast was delicious. Would come back!"
Canada
Natalie
The price is CA $241
CA $269 total
includes taxes & fees
Oct 1 - Oct 2
Hampton Inn Boston Bedford Burlington
A Holiday Inn Express hotel with a covered entrance, multiple floors, and a landscaped garden area.

11. Holiday Inn Express Boston - Saugus by IHG

Holiday Inn Express Boston - Saugus by IHG
3.0 star property
Saugus
8.6 out of 10, Excellent, (1,201 reviews)
"Great hotel, very clean and the breakfast was good!"
United States
Kelly
The price is CA $279
CA $311 total
includes taxes & fees
Sep 29 - Sep 30
Holiday Inn Express Boston - Saugus by IHG
A Hilton Garden Inn with a symmetrical facade, large entrance, and a covered walkway.

12. Hilton Garden Inn Boston/Waltham

Hilton Garden Inn Boston/Waltham
3.5 star property
Waltham
9.0 out of 10, Wonderful, (1,002 reviews)
"Nice place to stay"
United States
iram
The price is CA $181
CA $203 total
includes taxes & fees
Oct 4 - Oct 5
Hilton Garden Inn Boston/Waltham
A modern building with a 'Welcome' sign, a flag, and a blue van parked in front.

13. Hampton Inn & Suites Boston/Waltham

Hampton Inn & Suites Boston/Waltham
3.0 star property
Waltham
9.4 out of 10, Exceptional, (2,023 reviews)
"Well maintained property with great staff."
United States
Christopher
The price is CA $190
CA $212 total
includes taxes & fees
Oct 4 - Oct 5
Hampton Inn & Suites Boston/Waltham
A modern building with a covered entrance, multiple windows, and a parking lot.

14. The Inn on Arsenal

The Inn on Arsenal
2.5 star property
Watertown
8.0 out of 10, Very good, (434 reviews)
"Clean room, air conditioned and comfortable and super kind staff!"
United States
SEMORA
The price is CA $157
CA $175 total
includes taxes & fees
Sep 28 - Sep 29
The Inn on Arsenal
A multi-story building with a sign reading "Embassy Suites."

15. Embassy Suites by Hilton Boston Waltham

Embassy Suites by Hilton Boston Waltham
3.5 star property
Waltham
8.2 out of 10, Very good, (3,020 reviews)
"Great place to stay"
United States
Wesly
The price is CA $180
CA $201 total
includes taxes & fees
Sep 27 - Sep 28
Embassy Suites by Hilton Boston Waltham
A modern building with a courtyard, benches, and flower beds.

16. Porter Square Hotel

Porter Square Hotel
3.0 star property
Porter Square
9.2 out of 10, Wonderful, (1,000 reviews)
"Great place to stay!"
United States
Gerardo
The price is CA $267
CA $310 total
includes taxes & fees
Oct 12 - Oct 13
Porter Square Hotel
A modern hotel with a prominent 'Hyatt House' sign, featuring a symmetrical facade, large windows, and a landscaped entrance area.

17. HYATT house Boston/Waltham

HYATT house Boston/Waltham
3.0 star property
Waltham
9.0 out of 10, Wonderful, (1,139 reviews)
"Always a wonderful stay"
United States
Sarah
The price is CA $219
CA $245 total
includes taxes & fees
Oct 4 - Oct 5
HYATT house Boston/Waltham
A hotel with a large glass facade, a visible entrance, and a mailbox on the sidewalk.

18. Hotel 1868

Hotel 1868
3.5 star property
Agassiz
9.6 out of 10, Exceptional, (1,011 reviews)
"It was a great location and the staff were lovely."
United States
Margaret
The price is CA $303
CA $352 total
includes taxes & fees
Oct 12 - Oct 13
Hotel 1868
A Courtyard by Marriott hotel with a modern facade, multiple floors, and a well-lit entrance.

19. Courtyard by Marriott Boston Billerica/Bedford

Courtyard by Marriott Boston Billerica/Bedford
3.0 star property
Billerica
9.0 out of 10, Wonderful, (1,000 reviews)
"The grounds were very clean and the rooms were comfortable."
United States
CAROLYN
The price is CA $160
CA $179 total
includes taxes & fees
Oct 4 - Oct 5
Courtyard by Marriott Boston Billerica/Bedford
A modern building with a prominent 'CAMBRIA' sign, featuring a multi-story structure with large windows and a flat roof.

20. Cambria Hotel Boston Somerville

Cambria Hotel Boston Somerville
3.0 star property
Spring Hill
9.8 out of 10, Exceptional, (1,003 reviews)
"Fantastic hotel and great location!"
United States
Mary
The price is CA $346
CA $386 total
includes taxes & fees
Oct 4 - Oct 5
Cambria Hotel Boston Somerville
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

Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

10/10 Excellent
"Great clean"
Amanda 1-night trip
Posted 1 hour ago
Omni Boston Hotel at the Seaport

Find out more about Winchester

Winchester Houseboats information

Number of reviews
16,173
Accommodation
14 Houseboats
Lowest Price
CA $175
Highest Price
CA $386

Frequently asked questions

How much do houseboats in Winchester cost?
Houseboats in Winchester range between CA $175 and CA $386 per night. These unique getaways combine unrivaled access to the water with the comforts you need at a surprisingly affordable price. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many houseboats are there in Winchester?
Winchester has 14 houseboats to choose from for your next vacay on the water. Just key in your travel dates and destination and lock in your favorite floating escape.
Why book your houseboat in Winchester with Expedia?
Traveling shouldn't be hard, so if you're searching for houseboats at a competitive rate, Expedia can help. Save money and pick a smaller option with rustic charm, or book a luxury vessel and treat your crew.
What is there to do in Winchester near my houseboat?
The ideal travel accessory is a well-planned itinerary. Winter Pond is a wonderful spot to kick-start your adventures in Winchester.

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