Search Houseboats in Winchester from CA $157

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Check prices for these dates

Next weekend
Apr 4 - Apr 6
In two weeks
Apr 11 - Apr 13
In one month
Apr 25 - Apr 27
In two months
May 23 - May 25

Browse Select Winchester Houseboats

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 $358
CA $887 total
includes taxes & fees
Apr 22 - Apr 23
Fun houseboat. Walk to Boston attractions WIFI
"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, (213)
"My husband and I stayed here and were drawn to this unique property. It did not disappoint! Staff was lovely, everything was super clean, and you can't beat the location"
The price is CA $286
CA $517 total
includes taxes & fees
Apr 8 - Apr 9
"Travelers' Choice Award" Green Turtle I Houseboat in Boston Harbor!
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 $193
CA $742 total
includes taxes & fees
Mar 27 - Mar 28
Houseboat in Boston Harbor Wifi A/C /Heat Be rocked to sleep
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
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, (79)
"We enjoyed our stay here so much! The boat itself was very clean and had all the amenities we needed. The location is amazing - right in the middle of everything. We walked to most of our destinations. We highly recommend staying here. "
The price is CA $157
CA $638 total
includes taxes & fees
Mar 30 - Mar 31
Charlestown Houseboat Walk to attractions Be rocked to sleep
"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, (33)
"Had a great long St.Patricks weekend at the Green Turtle so happy we found this place instead of the normal hotel stay. Will be back!"
The price is CA $286
CA $510 total
includes taxes & fees
Apr 8 - Apr 9
"Travelers Choice Award" "Best of Boston" Green Turtle Houseboat Suite #2
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. "
The price is CA $445
CA $789 total
includes taxes & fees
Apr 15 - Apr 16
Capricornus: Oceanside Vacation
"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
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. "
The price is CA $420
CA $730 total
includes taxes & fees
Apr 3 - Apr 4
Endless Summer: Oceanside Views
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
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
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
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 $401
CA $707 total
includes taxes & fees
Mar 31 - Apr 1
Spacious & Comfy 2BR Yacht - Fully Heated - On Freedom Trail, Walk to Downtown
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

Maverick Suites at 28 Fenway
Deluxe Studio Suite (2nd Floor - Unit 202) | Living area

Maverick Suites at 28 Fenway

3.0 star property
9.0 out of 10, Wonderful, (174)
"Great location, short walk to parking. Very quiet and clean!!"
The price is CA $146
CA $307 total
includes taxes & fees
Mar 30 - Mar 31
Maverick Suites at 28 Fenway
Sonder 907 Main
Interior

Sonder 907 Main

4.0 star property
8.2 out of 10, Very good, (448)
"Very claen"
The price is CA $241
CA $280 total
includes taxes & fees
Mar 29 - Mar 30
Sonder 907 Main
Temple Place Suites
Deluxe Studio

Temple Place Suites

2.5 star property
6.8 out of 10, (192)
"The bed is super comfortable, self check in instructions are clear. Microwave, fridge, hairdryer and coffee maker all work excellently. The only downside is the shower hot water takes forever to start, and the heater is very noisy. It’s also close to the road, so the noises from the construction and roads are very noisy. Love the fact there’s elevator. "
The price is CA $153
CA $255 total
includes taxes & fees
Mar 27 - Mar 28
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 $157 and CA $445 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 15 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?
Expedia’s filters make it easy to find cheap houseboats in Winchester. Tailor your search by your budget and star rating — lower-rated houseboats won’t hit your bank balance as hard. You can also sign up for Expedia Rewards to reel in discounts on your floating home.
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.