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Check prices for these dates

Next weekend
13 Nov - 15 Nov
In two weeks
20 Nov - 22 Nov
In one month
4 Dec - 6 Dec
In two months
1 Jan - 3 Jan

Our top choices for Winchester houseboats

A white building with a blue roof, a wooden dock, and a metal staircase leading to a platform.

1. Fun houseboat. Walk to Boston attractions WIFI

Fun houseboat. Walk to Boston attractions WIFI
Boston
9.8 out of 10, Exceptional, (120 reviews)
"The houseboat was great! Everyone was super friendly and helpful. Can’t wait for our next stay!"
United States
Frank M.
The price is AED 496
AED 1,782 total
includes taxes & fees
7 Dec - 8 Dec
Fun houseboat. Walk to Boston attractions WIFI
A docked boat with a white cabin and a blue roof, connected to a pier with a wooden deck.

2. 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, (213 reviews)
"Wonderful brief stay!"
United States
Marie T.
The price is AED 441
AED 1,854 total
includes taxes & fees
7 Dec - 8 Dec
Houseboat in Boston Harbor Wifi A/C /Heat Be rocked to sleep
A waterfront building with a sign reading "Turtle," featuring a dock with red chairs and potted plants.

3. 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, (79 reviews)
"Great communication. The atmosphere was beautiful. Love all the baked goods"
United States
VIaney
The price is AED 1,102
AED 1,837 total
includes taxes & fees
4 Dec - 5 Dec
Unique Boston Harbor Houseboat Suite 2 - Experience near the Freedom Trail -AC
A marina with boats docked at the pier, reflecting the sunset sky.

4. 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, (142 reviews)
"Enjoyable stay"
United States
Carlos B.
The price is AED 1,405
AED 2,569 total
includes taxes & fees
10 Nov - 11 Nov
Boston Harbor Waterfront Yacht Escape near Freedom Trail 2B/2B sleeps 6 AC/Heat
A building with a sign reading "GREEN TURTLE" and a dock with red chairs.

5. 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, (268 reviews)
"The Houseboat was well appointed and clean. The hosts were very kind and left various drinks and breakfast items for us to enjoy. We enjoyed our stay there."
United States
D K
The price is AED 988
AED 1,782 total
includes taxes & fees
8 Nov - 9 Nov
Romantic Boston Harbor Houseboat Stay for 2 people. A/C. Close to Freedom Trail.
A houseboat docked at a pier with a clear sky, surrounded by water and a building with multiple balconies.

6. The Wave

The Wave
North End
10.0 out of 10, Exceptional, (3 reviews)
"location to walkable attractions, comfy beds and great host communications and assistance. Loved staying on the water in a houseboat!"
United States
Jodie
The price is AED 1,058
AED 1,820 total
includes taxes & fees
10 Nov - 11 Nov
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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Learn more about Winchester

Stroll along the shores of Mystic Lake, where locals gather for picnics and kayaking on sunny afternoons. History buffs can explore the Wright-Locke Farm, learning about sustainable agriculture while kids enjoy the farm animals and nature trails.

See all hotels in Winchester
An aerial view of a town with a lake, church steeples, and a bridge.

Top reviews in Winchester

A modern hotel entrance with a covered walkway, a glass facade, and a landscaped area with shrubs and trees.
Best Western Plus New Englander

Best Western Plus New Englander

Best Western Plus New Englander
Woburn

10/10 Excellent

The place was very clean it was beautiful scenery the staff helped us when we were looking for things
United States
Darlene
Reviewed November 4, 2026
Best Western Plus New Englander

Frequently Asked Questions

How much do houseboats in Winchester cost?

Houseboats in Winchester range between AED 440 and AED 1,404 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 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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