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Compare 15 Houseboats in Winchester with updated reviews, rates, and availability.

Charlestown Houseboat Walk to attractions Be rocked to sleep
Property grounds

Charlestown Houseboat Walk to attractions Be rocked to sleep

9.6 out of 10, Exceptional, (77)
"We loved staying on this houseboat. It was kind of like an adventure inside of an adventure. The only thing I would have changed (if I had the ability) was the weather. Our stay was in November (we were there for an event), so it was chilly. Next time we will stay when it's warmer, so we can enjoy coffee (by morning) and wine (by evening) out on the houseboat's deck. Our greeter was very helpful with the houseboat orientation and with walking directions from the boat. The location was really...
Charlestown Houseboat Walk to attractions Be rocked to sleep
Boston Harbor Yacht, AC/Heat, Walk to North End WiFi
Why stay anywhere else when visiting Boston?

Boston Harbor Yacht, AC/Heat, Walk to North End WiFi

9.6 out of 10, Exceptional, (130)
"The location is awesome, you can walk to the USS Constitution and the ferry to the north end. Boat is very nice. The check in was amazing. Some advice- it is a steep step climb to the boat so pack accordingly (our heavy suitcases were a challenge but was workable…use duffles if you can (we were on the road for a while so this was on us). The only other thing to note is the stove does not work, we bought stuff to cook but it is just a microwave. Overall, awesome stay. "
Boston Harbor Yacht, AC/Heat, Walk to North End WiFi
Houseboat in Boston Harbor Wifi A/C /Heat Be rocked to sleep
The Blue Pearl

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

9.8 out of 10, Exceptional, (177)
"Clean and comfortable! Loved the gentle rocking!"
The price is SAR 582
SAR 2,030 total
includes taxes & fees
25 Dec - 26 Dec
Houseboat in Boston Harbor Wifi A/C /Heat Be rocked to sleep
Endless Summer: Oceanside Views
Property grounds

Endless Summer: Oceanside Views

10.0 out of 10, Exceptional, (18)
"Such a unique and peaceful spot near everything that the North End has to offer. I would definitely rebook & recommend to others. "
Endless Summer: Oceanside Views
Stay aboard, the "Rita V", our 34 Ft Silverton Convertible Motoryacht
Marina

Stay aboard, the "Rita V", our 34 Ft Silverton Convertible Motoryacht

9.4 out of 10, Exceptional, (15)
"Great experience. I would stay here again, and hope to, many times over. Marina (building on right as you drive in, before larger restaurant building) has clean and comfortable full bathrooms that make this a great option."
Stay aboard, the "Rita V", our 34 Ft Silverton Convertible Motoryacht
Poseidon's Escape: Ocean Retreat
Outdoor dining

Poseidon's Escape: Ocean Retreat

8.8 out of 10, Excellent, (8)
"This review is about the boat we actually stayed on, Stars Hollow. We booked Poseidon's Escape but about 2 weeks before we were scheduled to arrive they emailed us notifying us that the boat had been removed from the harbor and substituted Stars Hollow boat. We enjoyed staying on a boat and this harbor is in the perfect spot for walking to everywhere. The subway is very close. We went in early October and it got a little chilly. There was no heat in the boat and there was only one blanket in...
Poseidon's Escape: Ocean Retreat
"Travelers' Choice Award" Green Turtle I Houseboat in Boston Harbor!
Marina

"Travelers' Choice Award" Green Turtle I Houseboat in Boston Harbor!

10.0 out of 10, Exceptional, (209)
"I enjoyed it. "
The price is SAR 751
SAR 1,352 total
includes taxes & fees
23 Dec - 24 Dec
"Travelers' Choice Award" Green Turtle I Houseboat in Boston Harbor!
"Travelers Choice Award" Spacious 2 bedrm 45 ft yacht close to the Freedom Trail
Green Turtle II - Your own private 45 foot yacht

"Travelers Choice Award" Spacious 2 bedrm 45 ft yacht close to the Freedom Trail

10.0 out of 10, Exceptional, (104)
"Everything about our stay was wonderful. Perfect location. We could walk everywhere. Our hosts were warm and wonderful and we enjoyed the yacht. Perfect after a long day sight seeing!!"
"Travelers Choice Award" Spacious 2 bedrm 45 ft yacht close to the Freedom Trail
Capricornus: Oceanside Vacation
Marina

Capricornus: Oceanside Vacation

9.6 out of 10, Exceptional, (22)
"We just spent one night but communication was great, listing was accurate. Would definitely stay again. "
Capricornus: Oceanside Vacation
Fun houseboat. Walk to Boston attractions WIFI
Fun way to visit Boston

Fun houseboat. Walk to Boston attractions WIFI

9.8 out of 10, Exceptional, (63)
"This houseboat is a perfect alternative to a hotel, such a fun experience. The location is perfect too. Highly recommend "
Fun houseboat. Walk to Boston attractions WIFI
Your Floating Suite in Boston Harbor
Marina

Your Floating Suite in Boston Harbor

9.8 out of 10, Exceptional, (56)
"We only stayed 2 nights but it was so conveniently located. Within walking distance to all our needs and not far from attractions. Didn't have to take the car anywhere. This was my first time using VRBO and all my questions were answered by the property owners including advice requests. Overall great experience"
Your Floating Suite in Boston Harbor
Spacious & Comfy 2BR Yacht - Fully Heated - On Freedom Trail, Walk to Downtown
Marina

Spacious & Comfy 2BR Yacht - Fully Heated - On Freedom Trail, Walk to Downtown

9.8 out of 10, Exceptional, (57)
"Chad and Holley were incredible hosts, they addressed all our needs immediately. They offered us an extensive list of local restaurants that were spot on. During our stay we experienced a couple of wonderful sunrises. The marina was calming with spectacular views of Boston during the night."
The price is SAR 890
SAR 1,649 total
includes taxes & fees
23 Dec - 24 Dec
Spacious & Comfy 2BR Yacht - Fully Heated - On Freedom Trail, Walk to Downtown
"Travelers Choice Award" "Best of Boston" Green Turtle Houseboat Suite #2
Green Turtle I Houseboat - 2 separate private suites in Boston Harbor!

"Travelers Choice Award" "Best of Boston" Green Turtle Houseboat Suite #2

9.8 out of 10, Exceptional, (32)
"Lovely days in Boston. We were sorry not to meet Jon. He sounds like a charming host. "
The price is SAR 751
SAR 1,352 total
includes taxes & fees
23 Dec - 24 Dec
"Travelers Choice Award" "Best of Boston" Green Turtle Houseboat Suite #2
Patriot: Three Story Vessel
Marina

Patriot: Three Story Vessel

9.2 out of 10, Wonderful, (5)
"The property was great! The communication was great. The refrigerator wasnt working properly and it was fixed almost immediately. We were very impressed by everything. Thank you, Boston!"
Patriot: Three Story Vessel
Romantic Getaway View the Boston Skyline, 10/15 minute drive to downtown.
Leather swivel chair

Romantic Getaway View the Boston Skyline, 10/15 minute drive to downtown.

Romantic Getaway View the Boston Skyline, 10/15 minute drive to downtown.
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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Other property types in Winchester

Sleep up to 4 Guest New Apt. 10 mins to Boston Easy to I-93
Private kitchen

Sleep up to 4 Guest New Apt. 10 mins to Boston Easy to I-93

7.4 out of 10, Good, (30)
"I give this place 3 stars, its a nice place with a good amount of room but there are a few issues. Our stay was Monday - Friday, just 2 adults. Pros - lots of room. Cons - no ac. There is a portable ac unit on wheels in the bedroom however, the exhaust vent goes behind a curtain to the window but not outside. There is no way to open the window for the exhaust vent to take the hot air outside so it just pumps all the hot air back into the room. Be prepared to wake up at 7:30am every morning...
Sleep up to 4 Guest New Apt. 10 mins to Boston Easy to I-93
Sonder 907 Main
Room

Sonder 907 Main

4.0 star property
8.2 out of 10, Very Good, (405)
"Perfect location!"
The price is SAR 483
SAR 560 total
includes taxes & fees
23 Dec - 24 Dec
Sonder 907 Main
Maverick Suites at 28 Fenway
Lobby sitting area

Maverick Suites at 28 Fenway

3.0 star property
9.0 out of 10, Wonderful, (156)
"Great stay. "
The price is SAR 372
SAR 795 total
includes taxes & fees
24 Dec - 25 Dec
Maverick Suites at 28 Fenway
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.

Frequently asked questions

How much do houseboats in Winchester cost?
Houseboats in Winchester range between SAR 582 and SAR 890 per night. These unique getaways combine adventure on the water with the comforts you need at an 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?
Reclaim your vacation days and pick from 15 houseboats in Winchester. For a romantic escape, a family getaway or anything in between, Expedia will help you find the right floating retreat in just a couple of clicks!
Why book your houseboat in Winchester with Expedia?
Expedia makes it a cinch to find houseboats in Winchester — from small, rustic options to real floating palaces! If you have a budget, choose how much you want to spend and your preferred star rating. We’ll help you find the right stay whatever your style of travel or plans.
How can I find cheap houseboats in Winchester?
If you’re looking for fantastic deals on houseboats in Winchester, you’ll want to add several filters to your search. You can sort your results by price so that the cheapest options appear first. Then, adjust your filters to match your budget. Expedia will help you find your dream floating stay whatever your bank balance or plans.