Winchester Town Hall and First Congregational Church at Winchester Center Historic District panorama in downtown Winchester, Massachusetts, USA.

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Check prices for these dates

In two weeks
10 Jul - 12 Jul
In two months
21 Aug - 23 Aug
In three months
18 Sep - 20 Sep
In four months
16 Oct - 18 Oct

Our top choices for Winchester houseboats

Exterior

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, (204 reviews)
"Perfect host, perfect spot, WORTH EVERY PENNY "
Canada
Jennifer E.
The price is AED 643
AED 2,107 total
includes taxes & fees
6 Jul - 7 Jul
Houseboat in Boston Harbor Wifi A/C /Heat Be rocked to sleep
Property grounds

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, (79 reviews)
"Overall very goodexperience..great neighborhood,views,very responsive owner..overall very good stay"
United States
jeff s.
The price is AED 1,159
AED 2,000 total
includes taxes & fees
30 Jun - 1 Jul
Spacious & Comfy 2BR/2Bath Yacht -Toasty Heat- On Freedom Trail-Walk to Downtown
Marina

"Travelers Choice Award" Spacious 2BD/2Bath Heat/AC 45 ft yacht Freedom Trail

"Travelers Choice Award" Spacious 2BD/2Bath Heat/AC 45 ft yacht Freedom Trail
Boston
10.0 out of 10, Exceptional, (124 reviews)
"Overall our stay was good!"
United States
Yan B.
The price is AED 1,653
AED 2,663 total
includes taxes & fees
29 Jun - 30 Jun
"Travelers Choice Award" Spacious 2BD/2Bath Heat/AC 45 ft yacht Freedom Trail
1 bedroom, iron/ironing board, travel crib, WiFi

Poseidon's Escape: Ocean Retreat

Poseidon's Escape: Ocean Retreat
Boston
9.2 out of 10, Wonderful, (15 reviews)
"This place was so great! It was comfy and perfect for our little get away!"
United States
Amanda R.
The price is AED 1,238
AED 2,082 total
includes taxes & fees
5 Jul - 6 Jul
Poseidon's Escape: Ocean Retreat
Outdoor dining

Best of Boston Houseboat Heat/AC in Boston Harbor Suite2 -Freedom Trail close by

Best of Boston Houseboat Heat/AC in Boston Harbor Suite2 -Freedom Trail close by
Thompson Square - Bunker Hill
10.0 out of 10, Exceptional, (63 reviews)
"Really loved our stay here. The room was well stocked with everything we could need and more. Would definitely book here again! "
United States
Daniel S.
The price is AED 1,157
AED 2,001 total
includes taxes & fees
27 Jun - 28 Jun
Best of Boston Houseboat Heat/AC in Boston Harbor Suite2 -Freedom Trail close by
Living area

Endless Summer: Oceanside Views

Endless Summer: Oceanside Views
Boston
10.0 out of 10, Exceptional, (42 reviews)
"This is a great location and very unique property. Perfect for my husband and I"
United States
Anonymous traveler
The price is AED 1,388
AED 2,279 total
includes taxes & fees
30 Jun - 1 Jul
Endless Summer: Oceanside Views
Terrace/patio

Best of Boston Houseboat Heat/AC in Boston Harbor Suite1 in Historic Navy Yard

Best of Boston Houseboat Heat/AC in Boston Harbor Suite1 in Historic Navy Yard
Charlestown
10.0 out of 10, Exceptional, (246 reviews)
"Loved this experience!!! Would book this again! So convenient to see Boston! "
United States
Ellen Z.
The price is AED 1,240
AED 2,113 total
includes taxes & fees
27 Jun - 28 Jun
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

Encore Boston Harbor

Encore Boston Harbor

8/10 Good
"You have to pay to use the gym, sauna and pool!"
Chirine 2-night trip
Posted 2 hours ago
Encore Boston Harbor

Frequently asked questions

How much do houseboats in Winchester cost?
Houseboats in Winchester range between AED 447 and AED 1,034 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 12 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.

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