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 $670

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Check prices for these dates

In two weeks
Jul 31 - Aug 2
In two months
Sep 11 - Sep 13
In three months
Oct 9 - Oct 11
In four months
Nov 6 - Nov 8

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, (205 reviews)
"Perfect host, perfect spot, WORTH EVERY PENNY "
Canada
Jennifer E.
The price is CA $226
CA $770 total
includes taxes & fees
Jul 19 - Jul 20
Houseboat in Boston Harbor Wifi A/C /Heat Be rocked to sleep
Outdoor dining

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, (67 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 CA $385
CA $692 total
includes taxes & fees
Aug 13 - Aug 14
Unique Boston Harbor Houseboat Suite 2 - Experience near the Freedom Trail -AC
Exterior

Fun houseboat. Walk to Boston attractions WIFI

Fun houseboat. Walk to Boston attractions WIFI
Boston
9.8 out of 10, Exceptional, (99 reviews)
"Beautiful place! Lots to do!"
United States
Julieann D.
The price is CA $300
CA $745 total
includes taxes & fees
Aug 16 - Aug 17
Fun houseboat. Walk to Boston attractions WIFI
Terrace/patio

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, (247 reviews)
"Loved this experience!!! Would book this again! So convenient to see Boston! "
United States
Ellen Z.
The price is CA $370
CA $670 total
includes taxes & fees
Jul 29 - Jul 30
Romantic Boston Harbor Houseboat Stay for 2 people. A/C. Close to Freedom Trail.
Exterior

The Wave

The Wave
North End
10.0 out of 10, Exceptional, (1 review)
The price is CA $552
CA $922 total
includes taxes & fees
Aug 9 - Aug 10
The Wave
Marina

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, (126 reviews)
"Overall our stay was good!"
United States
Yan B.
The price is CA $495
CA $852 total
includes taxes & fees
Aug 17 - Aug 18
Boston Harbor Waterfront Yacht Escape near Freedom Trail 2B/2B sleeps 6 AC/Heat
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, (81 reviews)
"Overall very goodexperience..great neighborhood,views,very responsive owner..overall very good stay"
United States
jeff s.
The price is CA $614
CA $989 total
includes taxes & fees
Aug 6 - Aug 7
Spacious & Comfy 2BR/2Bath Yacht -Toasty Heat- On Freedom Trail-Walk to Downtown
Living area

Endless Summer: Oceanside Views

Endless Summer: Oceanside Views
Boston
10.0 out of 10, Exceptional, (44 reviews)
"Absolutely beautiful and worth every penny. Sat for hours and just watched the boats, so relaxing. The boat was super clean and had everything you could possibly need. The steady rock of the boat was so amazing and peaceful. Planning an annual trip to Endless Summer."
United States
Megan T.
The price is CA $559
CA $893 total
includes taxes & fees
Jul 19 - Jul 20
Endless Summer: Oceanside Views
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 Parker House

Omni Parker House

10/10 Excellent
"The staff were top notch, but the property was too old for our taste so we couldn’t stay. Thank you for the smile and accommodation."
Imad 3-night trip
Posted less than an hour ago
Omni Parker House

Find out more about Winchester

Winchester Houseboats information

Number of reviews
472
Accommodation
16 Houseboats
Lowest Price
CA $670
Highest Price
CA $989

Frequently asked questions

How much do houseboats in Winchester cost?
Houseboats in Winchester range between CA $670 and CA $989 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 16 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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