Search Houseboats in Winchester

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Check prices for these dates

In two weeks
26 Dec - 28 Dec
In two months
6 Feb - 8 Feb
In three months
6 Mar - 8 Mar
In four months
3 Apr - 5 Apr

Our top choices for Winchester houseboats

Exterior
Fun houseboat. Walk to Boston attractions WIFI

Houseboat in Boston

Fun houseboat. Walk to Boston attractions WIFI
9.8 out of 10, Exceptional, (89)
"It was unique way to stay in the city"
United States
brian m.
The price is AED 367
AED 1,604 total
includes taxes & fees
11 Dec - 12 Dec
Fun houseboat. Walk to Boston attractions WIFI
Exterior
Houseboat in Boston Harbor Wifi A/C /Heat Be rocked to sleep

Houseboat in Charlestown

Houseboat in Boston Harbor Wifi A/C /Heat Be rocked to sleep
9.8 out of 10, Exceptional, (200)
"My husband and I had an excellent stay! It was very comfortable! I would highly recommend staying on The Blue Pearl and hope to stay there again. "
United States
Stacey W.
The price is AED 367
AED 1,748 total
includes taxes & fees
11 Dec - 12 Dec
Houseboat in Boston Harbor Wifi A/C /Heat Be rocked to sleep
Marina
Charlestown Houseboat Walk to attractions Be rocked to sleep

Houseboat in Thompson Square - Bunker Hill

Charlestown Houseboat Walk to attractions Be rocked to sleep
9.6 out of 10, Exceptional, (99)
"Location is great, houseboat is nice, we enjoyed our stay very much. "
United States
Ellen C.
The price is AED 367
AED 1,604 total
includes taxes & fees
5 Jan - 6 January 2026
Charlestown Houseboat Walk to attractions Be rocked to sleep
Marina
Best of Boston Houseboat Heat/AC in Boston Harbor Suite2 -Freedom Trail close by

Houseboat in Thompson Square - Bunker Hill

Best of Boston Houseboat Heat/AC in Boston Harbor Suite2 -Freedom Trail close by
10.0 out of 10, Exceptional, (57)
"Great houseboat experience! The check in process was fairly easy and the small kitchenette gave us the option to make coffee and have a quick breakfast in the mornings. "
United States
Michael K.
The price is AED 793
AED 1,397 total
includes taxes & fees
11 Dec - 12 Dec
Best of Boston Houseboat Heat/AC in Boston Harbor Suite2 -Freedom Trail close by
Marina
Best of Boston Houseboat Heat/AC in Boston Harbor Suite1 in Historic Navy Yard

Houseboat in Charlestown

Best of Boston Houseboat Heat/AC in Boston Harbor Suite1 in Historic Navy Yard
10.0 out of 10, Exceptional, (241)
"Very comfortable stay. Easy walk to ferry. Parking was great at the dock."
United States
Joseph E.
The price is AED 793
AED 1,397 total
includes taxes & fees
11 Dec - 12 Dec
Best of Boston Houseboat Heat/AC in Boston Harbor Suite1 in Historic Navy Yard
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

citizenM Boston North Station

citizenM Boston North Station

10/10 Excellent
"Clean rooms, staff was nice and very helpful, the view from the room was amazing."
Jessica 4-night trip
Posted 14 hours ago
citizenM Boston North Station

Frequently asked questions

How much do houseboats in Winchester cost?
Houseboats in Winchester range between AED 1,397 and AED 1,748 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.
How can I find cheap houseboats in Winchester?
If you're on the lookout for incredible deals on houseboats in Winchester, add a few filters to your search. Start by sorting your results by price so that the cheapest options appear at the top. Then, adjust your filters to match your budget. Also, make sure you join our free rewards program, One Key™, for exclusive member deals. Expedia can help you find your dream floating getaway whatever your budget or plans.