A town with a prominent church, a large building with a clock tower, and a mix of residential and commercial buildings surrounded by greenery.

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Check prices for these dates

In two weeks
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27
No exact matches found, but these alternatives could be just right

Recommended hotels in Winchester

Exterior

1. Hampton Inn Boston Woburn

Hampton Inn Boston Woburn
2.5 star property
Woburn
9.2 out of 10, Wonderful, (1,498 reviews)
"Always stay here when we come to the area. Great location and staff!"
United States
Charles Richard Losh
The price is CA $192
CA $215 total
includes taxes & fees
Sep 7 - Sep 8
Hampton Inn Boston Woburn
Exterior

2. Hilton Boston/Woburn

Hilton Boston/Woburn
3.5 star property
Woburn
8.6 out of 10, Excellent, (1,453 reviews)
"Very nice stay."
United States
Colin
The price is CA $208
CA $232 total
includes taxes & fees
Sep 13 - Sep 14
Hilton Boston/Woburn
Exterior

3. Holiday Inn Express Boston North-Woburn by IHG

Holiday Inn Express Boston North-Woburn by IHG
2.5 star property
Woburn
8.2 out of 10, Very good, (1,023 reviews)
"Everything was good, would definitely stay here again."
United States
Greg
The price is CA $139
CA $155 total
includes taxes & fees
Sep 13 - Sep 14
Holiday Inn Express Boston North-Woburn by IHG
Exterior

4. Crowne Plaza Boston - Woburn by IHG

Crowne Plaza Boston - Woburn by IHG
4.0 star property
Woburn
8.6 out of 10, Excellent, (1,093 reviews)
"Very clean hotel and staff were kind!"
United States
Shaina
The price is CA $180
CA $201 total
includes taxes & fees
Sep 11 - Sep 12
Crowne Plaza Boston - Woburn by IHG
Exterior

5. Hampton Inn Boston - Logan Airport

Hampton Inn Boston - Logan Airport
3.0 star property
Revere
8.2 out of 10, Very good, (5,574 reviews)
"The shuttle to and from the airport, great breakfast and comfortable room. Would stay here again!"
United States
Deborah
The price is CA $231
CA $258 total
includes taxes & fees
Sep 10 - Sep 11
Hampton Inn Boston - Logan Airport
Exterior

6. Hampton Inn Boston Logan Airport Chelsea

Hampton Inn Boston Logan Airport Chelsea
2.5 star property
Chelsea
9.0 out of 10, Wonderful, (3,218 reviews)
"Great stay!"
Canada
Galyna
The price is CA $246
CA $275 total
includes taxes & fees
Sep 13 - Sep 14
Hampton Inn Boston Logan Airport Chelsea
Exterior

7. Comfort Inn & Suites Logan International Airport

Comfort Inn & Suites Logan International Airport
2.5 star property
Revere
9.0 out of 10, Wonderful, (2,399 reviews)
"Location and airport shuttle was great"
United States
Jane
The price is CA $234
CA $270 total
includes taxes & fees
Sep 7 - Sep 8
Comfort Inn & Suites Logan International Airport
Exterior

8. Hyatt Place Boston/Seaport District

Hyatt Place Boston/Seaport District
3.0 star property
Seaport District
9.4 out of 10, Exceptional, (2,435 reviews)
"Great hotel in a great location lovely property will definitely stay again"
United Kingdom
Adam
The price is CA $275
CA $321 total
includes taxes & fees
Sep 7 - Sep 8
Hyatt Place Boston/Seaport District
Exterior

9. Holiday Inn Express Boston - Saugus by IHG

Holiday Inn Express Boston - Saugus by IHG
3.0 star property
Saugus
8.6 out of 10, Excellent, (1,207 reviews)
"great stay! nice hotel"
United States
Ryan
The price is CA $176
CA $196 total
includes taxes & fees
Sep 10 - Sep 11
Holiday Inn Express Boston - Saugus by IHG
Exterior

10. Staybridge Suites Boston - Burlington by IHG

Staybridge Suites Boston - Burlington by IHG
3.0 star property
Burlington
9.0 out of 10, Wonderful, (457 reviews)
"Very clean facility all around, Continental breakfast was perfect for our family."
United States
Danielle
The price is CA $223
CA $249 total
includes taxes & fees
Sep 8 - Sep 9
Staybridge Suites Boston - Burlington by IHG
Exterior

11. Embassy Suites Boston Logan Airport

Embassy Suites Boston Logan Airport
3.5 star property
East Boston
8.8 out of 10, Excellent, (2,600 reviews)
"Great stay, close to the airport."
United States
Maria Criselda
The price is CA $298
CA $347 total
includes taxes & fees
Sep 8 - Sep 9
Embassy Suites Boston Logan Airport
Exterior

12. Hilton Garden Inn Boston Logan Airport

Hilton Garden Inn Boston Logan Airport
3.0 star property
East Boston
9.2 out of 10, Wonderful, (2,282 reviews)
"Nice and clean hotel!! Super close to the airport!"
United States
Nicole Ann
The price is CA $282
CA $329 total
includes taxes & fees
Sep 7 - Sep 8
Hilton Garden Inn Boston Logan Airport
Exterior

13. Hampton by Hilton at the Boston Seaport District

Hampton by Hilton at the Boston Seaport District
3.0 star property
Seaport District
9.2 out of 10, Wonderful, (2,897 reviews)
"Very good place to stay."
United States
Darin
The price is CA $250
CA $292 total
includes taxes & fees
Sep 7 - Sep 8
Hampton by Hilton at the Boston Seaport District
Exterior

14. Courtyard by Marriott Boston Downtown/North Station

Courtyard by Marriott Boston Downtown/North Station
3.0 star property
West End
9.4 out of 10, Exceptional, (1,468 reviews)
"Excellent location , grate hotel"
United States
Jennifer
The price is CA $269
CA $314 total
includes taxes & fees
Sep 7 - Sep 8
Courtyard by Marriott Boston Downtown/North Station
Exterior

15. Archer Hotel Boston/Burlington

Archer Hotel Boston/Burlington
4.0 star property
Burlington
9.8 out of 10, Exceptional, (1,002 reviews)
"Clean modern hotel close to restaurants and convenience retail."
United States
JOHN
The price is CA $256
CA $286 total
includes taxes & fees
Sep 12 - Sep 13
Archer Hotel Boston/Burlington
Exterior

16. Hampton Inn & Suites Boston/Waltham

Hampton Inn & Suites Boston/Waltham
3.0 star property
Waltham
9.4 out of 10, Exceptional, (2,013 reviews)
"Our favorite place to stay"
United States
Julie
The price is CA $172
CA $192 total
includes taxes & fees
Sep 7 - Sep 8
Hampton Inn & Suites Boston/Waltham
Front of property

17. Quality Inn Boston - Revere

Quality Inn Boston - Revere
2.5 star property
Revere
7.6 out of 10, Good, (1,019 reviews)
"The staff was great and the breakfast was edible!"
United States
Nia
The price is CA $173
CA $193 total
includes taxes & fees
Sep 13 - Sep 14
Quality Inn Boston - Revere
Exterior

18. Hyatt Regency Boston Harbor

Hyatt Regency Boston Harbor
4.0 star property
East Boston
9.2 out of 10, Wonderful, (2,029 reviews)
"Great location and ideal for travel in and out of Logan."
United States
John Brendan
The price is CA $275
CA $355 total
includes taxes & fees
Sep 7 - Sep 8
Hyatt Regency Boston Harbor
Exterior

19. Seaport Hotel Boston

Seaport Hotel Boston
4.0 star property
Seaport District
9.6 out of 10, Exceptional, (4,958 reviews)
"Nice location and good accommodations."
United States
Cordell
The price is CA $262
CA $352 total
includes taxes & fees
Sep 20 - Sep 21
Seaport Hotel Boston
Front of property

20. Lakeside Inn

Lakeside Inn
2.0 star property
Wakefield
8.2 out of 10, Very good, (822 reviews)
"I really liked staying there definitely will be there again"
United States
Marc
The price is CA $124
CA $138 total
includes taxes & fees
Sep 14 - Sep 15
Lakeside Inn
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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Top Winchester Hotel Reviews

Harborside Inn Of Boston

Harborside Inn Of Boston

8/10 Good
"Beautiful and convenient"
Jacqueline 2-night trip
Posted less than an hour ago
Harborside Inn Of Boston

Find out more about Winchester

Winchester Cabin Rentals information

Number of reviews
20,563
Accommodation
0 Cabin Rentals
Lowest Price
CA $138
Highest Price
CA $355

Frequently asked questions

What are the best cabins near Winchester?
Ranging from small and quaint to spacious and luxurious, there are 52 cabins to choose from in and around Winchester. Top options include Fantastic 4 - Season Cabin At Baxter Lake and Cabin: Private Hot Tub, Walk To Pats Peak Ski Area.
Are there cheap cabins in Winchester?
Priced from CA $138 to CA $355 per night, getting away with the family has never been easier. Secure one of our cheap cabins in Winchester and enjoy the great outdoors without breaking the bank.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.
What are the best mountain cabins near Winchester?
If you're craving crisp air and superb views, spend your next break in a Winchester mountain cabin. Explore the rugged beauty around Cozy, Wooded, Waterfront, Mountain View Cabin On Silver Lake. This rental has all the ingredients for an enjoyable getaway, including a porch and a microwave oven. Or, experience a taste of the mountain lifestyle at Cabin: Private Hot Tub, Walk To Pats Peak Ski Area. It comes with a deck, a wood stove and more.
What are the best river cabins near Winchester?
If you're searching for a character-filled retreat surrounded by water and adventure, a Winchester river cabin is hard to go past. Unpack your bags at Rustic Cabin - Style On River Northwest Of Concord Nh Within Minutes Of Penecook and let all your problems float away downstream. Useful amenities here include on-site watersports and outdoor furniture. Another leading riverside option is The Windfall Off - Grid Cabin And Farm Stay. It comes with winery tours, outdoor furniture and more.
What are the best cabins with pools near Winchester?
If you love the thought of every day being a pool day, escape to Lighthouse - Q991 Near Sandy Gorgeous Ogunquit Beach 2 Bedroom Cabin By Redawning. It's one of our top cabin rentals with a pool and comes with amenities like a swimming pool and a barbecue grill. Cabin - Lighthouse - Q991by Getaway is another place to spend relaxing days poolside. A swimming pool, individually decorated rooms and good times are what you can expect here.
Can I find beach cabins near Winchester?
Enjoy sunset strolls along a beautiful shoreline when you choose a Winchester beach cabin rental. Sun and fun should be the only things on your mind at Beachfront Cottage, Very Quaint And Right On The Beach. This property comes with cycling and clothes washing facilities. Alternatively, toss your bag down and put your feet up at The Mermaid House @ Obc Cape Cod Beach Resort. Handy amenities here include on-site watersports and children's activities.
What are the best weekend cabin rentals in Winchester?
Whether you're planning a mini break with your honey or the whole crew, we'll help you locate the ideal weekend cabin getaway. One of our top picks? Fantastic 4 - Season Cabin At Baxter Lake. Featuring on-site watersports and a patio, you'll appreciate being surrounded by nature here. Beachfront Cottage, Very Quaint And Right On The Beach is another place where you can slow down for a while. Enjoy a few nights or more at this retreat which offers a patio and a barbecue grill.
What are the best cabin prices in Winchester?
If you'd rather save a few dollars on your stay, we've got some terrific deals on Winchester cabins that won't put a hole in your vacation budget. How does CA $138 a night sound?
Can I find log cabins in Winchester?
Begin your day with a cup of coffee in your peaceful log cabin and then enjoy some mountain biking and snowboarding. Sound dreamy? Then head for Cozy Updated Log Cabin With Mountain Views Close To Monadnock. Another getaway that comes with lots of character and comfort is Rustic Log Cabin On The Lake. Nearby activities like horse riding and cycling will add to your experience here.
What are the highest-rated cabins in Winchester?
With an impressive rating, it's no surprise why The Mermaid House @ Obc Cape Cod Beach Resort is a popular pick with Expedia travellers. Some useful amenities here include on-site watersports and a patio. The Crab House @obc Cape Cod Beach Resort is another fabulous option. Quality conveniences such as on-site watersports and a spa tub will help make your stay a comfy one.
Why should I book a cabin in Winchester?
For a vacation experience that's big on charm, home comforts and affordability, it's hard to top a cabin. Lose your city blues in the greenery of nature. From days spent rambling to peaceful evenings cuddled up by a campfire, cabins offer the perfect mix of excitement and relaxation. Check out the wonderful Winchester options right here on Expedia.
What are the top nature cabins in Winchester?
With plenty of charm and creature comforts, Rustic Cabin - Style On River Northwest Of Concord Nh Within Minutes Of Penecook is one of our favourite nature cabins in Winchester. But with a bunch of things to do and see close by, make sure you don't spend too much time indoors. Activities including nearby rafting and nearby kayaking are waiting. The Windfall Off - Grid Cabin And Farm Stay is another place where you can immerse yourself in nature. Nearby fishing and paddle boating are a few enjoyable ways to do it.

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