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

Search Houseboats in Winchester from CA $136

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Check prices for these dates

In two weeks
Sep 25 - Sep 27
In two months
Nov 6 - Nov 8
In three months
Dec 4 - Dec 6
In four months
Jan 1 - Jan 3

Our top choices for Winchester houseboats

Exterior

1. Houseboat in Boston Harbor Wifi A/C /Heat Be rocked to sleep

Houseboat in Boston Harbor Wifi A/C /Heat Be rocked to sleep
Charlestown
9.8 out of 10, Exceptional, (210 reviews)
"Such a quaint and quiet location. We loved staying on the pier. The boat was clean and tidy!! We would definitely stay there again!!"
United States
Angela L.
The price is CA $243
CA $793 total
includes taxes & fees
Sep 13 - Sep 14
Houseboat in Boston Harbor Wifi A/C /Heat Be rocked to sleep
Marina

2. Your Floating Suite in Boston Harbor

Your Floating Suite in Boston Harbor
Thompson Square - Bunker Hill
9.6 out of 10, Exceptional, (64 reviews)
"Most peaceful nights sleep I’ve gotten scenic & people very friendly "
United States
Kelly H.
The price is CA $194
CA $728 total
includes taxes & fees
Sep 8 - Sep 9
Your Floating Suite in Boston Harbor
Exterior

3. Fun houseboat. Walk to Boston attractions WIFI

Fun houseboat. Walk to Boston attractions WIFI
Boston
9.8 out of 10, Exceptional, (108 reviews)
"Rustic boathouse in a great central location ."
United States
William M.
The price is CA $197
CA $678 total
includes taxes & fees
Sep 8 - Sep 9
Fun houseboat. Walk to Boston attractions WIFI
Outdoor dining

4. Unique Boston Harbor Houseboat Suite 2 - Experience near the Freedom Trail -AC

Unique Boston Harbor Houseboat Suite 2 - Experience near the Freedom Trail -AC
Thompson Square - Bunker Hill
9.8 out of 10, Exceptional, (72 reviews)
"Great location and the host was very helpful for everything. Definitely I’m gonna stay here again."
United States
Sandy M.
The price is CA $372
CA $665 total
includes taxes & fees
Sep 13 - Sep 14
Unique Boston Harbor Houseboat Suite 2 - Experience near the Freedom Trail -AC
Property grounds

5. Spacious & Comfy 2BR/2Bath Yacht -Toasty Heat- On Freedom Trail-Walk to Downtown

Spacious & Comfy 2BR/2Bath Yacht -Toasty Heat- On Freedom Trail-Walk to Downtown
Thompson Square - Bunker Hill
9.8 out of 10, Exceptional, (87 reviews)
"The atmosphere was very relaxing. Everything was walking distance. We had a good time."
United States
Sandra Hatz J.
The price is CA $437
CA $753 total
includes taxes & fees
Sep 10 - Sep 11
Spacious & Comfy 2BR/2Bath Yacht -Toasty Heat- On Freedom Trail-Walk to Downtown
Terrace/patio

6. Romantic Boston Harbor Houseboat Stay for 2 people. A/C. Close to Freedom Trail.

Romantic Boston Harbor Houseboat Stay for 2 people. A/C. Close to Freedom Trail.
Charlestown
10.0 out of 10, Exceptional, (254 reviews)
"Loved this experience!!! Would book this again! So convenient to see Boston! "
United States
Ellen Z.
The price is CA $345
CA $635 total
includes taxes & fees
Sep 8 - Sep 9
Romantic Boston Harbor Houseboat Stay for 2 people. A/C. Close to Freedom Trail.
Marina

7. Boston Harbor Waterfront Yacht Escape near Freedom Trail 2B/2B sleeps 6 AC/Heat

Boston Harbor Waterfront Yacht Escape near Freedom Trail 2B/2B sleeps 6 AC/Heat
Boston
10.0 out of 10, Exceptional, (133 reviews)
"I reserved the Green Turtle for out-of-town guests over Memorial Day weekend and will do so again. They will thrilled to stay on the water their first time visiting Boston and found the boat comfortable and restful."
United States
Gale P.
The price is CA $556
CA $1,004 total
includes taxes & fees
Sep 30 - Oct 1
Boston Harbor Waterfront Yacht Escape near Freedom Trail 2B/2B sleeps 6 AC/Heat
Exterior

8. The Wave

The Wave
North End
10.0 out of 10, Exceptional, (1 review)
The price is CA $571
CA $945 total
includes taxes & fees
Sep 13 - Sep 14
The Wave
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

The Revolution Hotel

The Revolution Hotel

10/10 Excellent
"Excellent value for the price, and located in the very hip South End of Boston."
Michael 1-night trip
Posted 1 hour ago
The Revolution Hotel

Find out more about Winchester

Winchester Houseboats information

Number of reviews
13,532
Accommodation
14 Houseboats
Lowest Price
CA $136
Highest Price
CA $314

Frequently asked questions

How much do houseboats in Winchester cost?
Houseboats in Winchester range between CA $136 and CA $314 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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