Search Houseboats in Winchester from CA $99

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Check prices for these dates

Next weekend
Feb 28 - Mar 2
In two weeks
Mar 7 - Mar 9
In one month
Mar 21 - Mar 23
In two months
Apr 18 - Apr 20

Browse Select Winchester Houseboats

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

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

9.8 out of 10, Exceptional, (179)
"Amazing location and superior communication. "
The price is CA $206
CA $758 total
includes taxes & fees
Mar 2 - Mar 3
Houseboat in Boston Harbor Wifi A/C /Heat Be rocked to sleep
"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 CA $319
CA $556 total
includes taxes & fees
Feb 23 - Feb 24
"Travelers' Choice Award" Green Turtle I Houseboat in Boston Harbor!
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, (78)
"I so happened to pick the coldest week but had no choice as was visiting. Everything was very clean and easy process coming into and leaving properly. I would definitely stay here again but in Spring season. Host was easily accessible to communicate with. "
The price is CA $99
CA $565 total
includes taxes & fees
Feb 25 - Feb 26
Charlestown Houseboat Walk to attractions Be rocked to sleep
Fun houseboat. Walk to Boston attractions WIFI
Interior

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 "
The price is CA $206
CA $702 total
includes taxes & fees
Mar 2 - Mar 3
Fun houseboat. Walk to Boston attractions WIFI
Boston Harbor Yacht, AC/Heat, Walk to North End WiFi
Interior

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
Endless Summer: Oceanside Views
Interior

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
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
Stay aboard, the "Rita V", our 34 Ft Silverton Convertible Motoryacht
1 bedroom, WiFi, bed sheets

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

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

"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 CA $319
CA $549 total
includes taxes & fees
Feb 22 - Feb 23
"Travelers Choice Award" "Best of Boston" Green Turtle Houseboat Suite #2
Patriot: Three Story Vessel
TV, fireplace

Patriot: Three Story Vessel

9.2 out of 10, Wonderful, (5)
"My coworkers and I were in town for a convention. Instead of staying in a hotel, we opted for this unique lodging opportunity. BEST DECISION EVER! Great accommodations in a terrific area. 100% recommended. "
Patriot: Three Story Vessel
Spacious & Comfy 2BR Yacht - Fully Heated - On Freedom Trail, Walk to Downtown
Miscellaneous

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 CA $527
CA $876 total
includes taxes & fees
Mar 13 - Mar 14
Spacious & Comfy 2BR Yacht - Fully Heated - On Freedom Trail, Walk to Downtown
Capricornus: Oceanside Vacation
Interior

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

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

Sonder 907 Main
Interior

Sonder 907 Main

4.0 star property
8.2 out of 10, Very good, (433)
"Clean, spacious room/bathroom, convenient. "
The price is CA $164
CA $190 total
includes taxes & fees
Feb 23 - Feb 24
Sonder 907 Main
No. 284 powered by Sonder
Exterior

No. 284 powered by Sonder

4.0 star property
9.4 out of 10, Exceptional, (868)
"my favorite stay ever. i loved my stay and everything about it and can’t wait to come back soon. "
The price is CA $218
CA $257 total
includes taxes & fees
Feb 24 - Feb 25
No. 284 powered by Sonder
Temple Place Suites
Deluxe Studio

Temple Place Suites

2.5 star property
6.8 out of 10, (182)
"Insane lil spot for seeing Boston and surrounding areas!"
The price is CA $122
CA $219 total
includes taxes & fees
Feb 23 - Feb 24
Temple Place Suites
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 CA $99 and CA $527 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.
What is there to do in Winchester near my houseboat?
The best travel accessory is a well-planned to-do list. Winter Pond is an excellent place to begin your adventures in Winchester.