Title: Book the Best LAKESIDE Hotels in Winchester in 2026 | Expedia.ca

[Hotels in Winchester](https://expedia.ca/Winchester-Hotels.d3000447144.Travel-Guide-Hotels)[Vacation Rentals in Winchester](https://expedia.ca/Winchester-Vacation-Rentals.d3000447144.Travel-Guide-VacationRentals)[Winchester Car Rentals](https://expedia.ca/Car-Rentals-In-Winchester.d3000447144.Car-Rental-Guide)[Winchester Vacation Packages](https://expedia.ca/Winchester.d3000447144.Destination-Travel-Guides)

![Winchester, New Hampshire in winter ](https://images.trvl-media.com/place/3000447144/3e6a6279-072b-4adb-98ce-884d4d6659f9.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

![](https://images.trvl-media.com/place/3000447144/3e6a6279-072b-4adb-98ce-884d4d6659f9.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

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## Check availability on Winchester Lake Hotels

Tonight

[Feb 5 - Feb 6](https://www.expedia.ca/Hotel-Search?regionId=3000447144&startDate=2026-02-05&endDate=2026-02-06&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Feb 6 - Feb 7](https://www.expedia.ca/Hotel-Search?regionId=3000447144&startDate=2026-02-06&endDate=2026-02-07&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

This weekend

[Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=3000447144&startDate=2026-02-06&endDate=2026-02-08&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Feb 13 - Feb 15](https://www.expedia.ca/Hotel-Search?regionId=3000447144&startDate=2026-02-13&endDate=2026-02-15&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Winchester hotels on the lake

![Terrace/patio](https://images.trvl-media.com/lodging/3000000/2210000/2205700/2205666/6a4870a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/3000000/2210000/2205700/2205666/01fdfd63.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds](https://images.trvl-media.com/lodging/3000000/2210000/2205700/2205666/8a97a85f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fireplace](https://images.trvl-media.com/lodging/3000000/2210000/2205700/2205666/56f95948.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Maguire House Bed & Breakfast

[](https://www.expedia.ca/Leominster-Hotels-The-Maguire-House-Bed-Breakfast.h2205666.Hotel-Information)

Ashburnham

10/10

Exceptional

(36 reviews)

"Wonderful bed and breakfast - and remarkable hosts! Definitely worth booking if you plan to be in the area. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Ranjit

CA $375

CA $375 total

includes taxes & fees

Feb 26 - Feb 27

[](https://www.expedia.ca/Leominster-Hotels-The-Maguire-House-Bed-Breakfast.h2205666.Hotel-Information)

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.

[View all properties](https://expedia.ca/Hotel-Search?startDate=2026-02-19&endDate=2026-02-20&regionId=3000447144&adults=2&location_highlights_explore=on_lake&sort=RECOMMENDED&openPlayBack=true)

## Top Winchester Hotel Reviews

![Riverside Hotel, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/3000000/2880000/2877400/2877372/34b58580_y.jpg)

### Riverside Hotel, an Ascend Collection Hotel

10/10 Excellent

"Yes"

[](https://expedia.ca/Keene-Hotels-Riverside-Hotel.h2877372.Hotel-Information)

## Frequently asked questions

### Why book your lakeside hotel in Winchester with Expedia?

### How can I find cheap lakeside hotels in Winchester?

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