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 Winchester Cottages

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Aug 28 - Aug 30
In two months
Oct 9 - Oct 11
In three months
Nov 6 - Nov 8
In four months
Dec 4 - Dec 6

Our top choices for Winchester cottages

Exterior

1. Witchy Hideaway Cottage; Close to Beaches, Salem & Train to Boston

Witchy Hideaway Cottage; Close to Beaches, Salem & Train to Boston
Beverly
10.0 out of 10, Exceptional, (6 reviews)
"Great little spot if you need to stay close to downtown Salem. Would recommend!"
United States
Corey W.
$310 nightly
The price is $346
Aug 23 - Aug 24
Total with taxes and fees
Witchy Hideaway Cottage; Close to Beaches, Salem & Train to Boston
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
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winchester Hotel Reviews

Seaport Hotel Boston

Seaport Hotel Boston

10/10 Excellent
"I had booked my room in advance and requested adjoining rooms as we where traveling as a family Well thank god I did not had small children because they did not give me adjoining room we had 3 separate rooms and we are a family of 5 They claim they where booked and adjoining rooms are not guaranteed they did but us on the same floor that was good the rooms where clean and we where comfortable and it was quiet so I’m thankful for that Other than that the staff is very friendly it’s clean we requested a microwave and it was in our room in no time the breakfast was amazing the bar was amazing Dining wasn’t much of an option as I’m allergic to seafood and they don’t offer much of what we would like to eat . But is a beautiful hotel and location"
IRMA 3-night trip
Posted less than an hour ago
Seaport Hotel Boston

Find out more about Winchester

Winchester Cottages information

Number of reviews
6
Accommodation
34 Cottages
Lowest Price
$346
Highest Price
$346

Frequently asked questions

Why book your cottage in Winchester with Expedia?
Expedia has some great cottages in Winchester, so start planning for an unforgettable stay on nature's doorstep. If you have a budget in mind, click on how much you'd like to spend and the preferred star rating of your property. Or, use our filters to search for cottages with free WiFi or a kitchen. We'll help you find a suitable place whatever your plans or style of travel.
How can I find cheap cottages in Winchester?
Expedia is here to help you easily locate cheap cottages in Winchester. To discover your ideal stay in a few quick keystrokes, use our handy filter tool to refine your search by amenities, budget and star rating.
What is there to do in Winchester near my cottage?
The most useful travel accessory is a well-thought-out travel plan. Winter Pond is a wonderful spot to kick-start your sightseeing in Winchester.

Explore a world of travel with Expedia