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
Jul 31 - Aug 2
In two months
Sep 11 - Sep 13
In three months
Oct 9 - Oct 11
In four months
Nov 6 - Nov 8
No exact matches found, but these alternatives could be just right

Recommended hotels in Winchester

Exterior

Best Western Plus New Englander

Best Western Plus New Englander
2.5 star property
Woburn
8.6 out of 10, Excellent, (1,079 reviews)
"Nice staff, good for a quick stay!!!"
United States
Madelin
The price is CA $167
CA $187 total
includes taxes & fees
Jul 26 - Jul 27
Best Western Plus New Englander
Exterior

Crowne Plaza Boston - Woburn by IHG

Crowne Plaza Boston - Woburn by IHG
3.5 star property
Woburn
8.6 out of 10, Excellent, (1,024 reviews)
"Very friendly staff and clean rooms"
United States
Yesenia
The price is CA $151
CA $168 total
includes taxes & fees
Aug 10 - Aug 11
Crowne Plaza Boston - Woburn by IHG
Exterior

Hampton Inn Boston Woburn

Hampton Inn Boston Woburn
2.5 star property
Woburn
9.2 out of 10, Wonderful, (1,457 reviews)
"Great place, convenient area sipping food and everything else. Hotel was excellent"
Canada
Michele
The price is CA $185
CA $207 total
includes taxes & fees
Aug 2 - Aug 3
Hampton Inn Boston Woburn
Exterior

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, (1,159 reviews)
"Clean and nice hotel. Front desk people very nice and friendly."
United States
rosario
The price is CA $149
CA $167 total
includes taxes & fees
Aug 9 - Aug 10
Holiday Inn Express Boston - Saugus by IHG
Front of property

Lakeside Inn

Lakeside Inn
2.0 star property
Wakefield
7.6 out of 10, Good, (2,385 reviews)
"Clean place, very helpful staff, the breakfast was the best part!"
United States
Ryan
The price is CA $127
CA $142 total
includes taxes & fees
Jul 20 - Jul 21
Lakeside Inn
Front of property - evening/night

Sonesta Simply Suites Boston Burlington

Sonesta Simply Suites Boston Burlington
2.0 star property
Burlington
8.8 out of 10, Excellent, (394 reviews)
"Very clean, affordable, nice amenities in a nice area."
United States
Frances
The price is CA $200
CA $223 total
includes taxes & fees
Aug 1 - Aug 2
Sonesta Simply Suites Boston Burlington
Exterior

Archer Hotel Boston/Burlington

Archer Hotel Boston/Burlington
4.0 star property
Burlington
9.8 out of 10, Exceptional, (1,000 reviews)
"All around perfect stay"
United States
Tahjwayne
The price is CA $241
CA $269 total
includes taxes & fees
Aug 7 - Aug 8
Archer Hotel Boston/Burlington
Exterior

Hampton Inn Boston Bedford Burlington

Hampton Inn Boston Bedford Burlington
2.5 star property
Billerica
9.2 out of 10, Wonderful, (1,011 reviews)
"Great location and very clean."
United States
Kenneth
The price is CA $183
CA $205 total
includes taxes & fees
Aug 2 - Aug 3
Hampton Inn Boston Bedford Burlington
Exterior

HYATT house Boston/Waltham

HYATT house Boston/Waltham
3.0 star property
Waltham
9.0 out of 10, Wonderful, (1,097 reviews)
"Very nice room spacious and clean I had a great stay ."
United States
taronna
The price is CA $188
CA $210 total
includes taxes & fees
Jul 24 - Jul 25
HYATT house Boston/Waltham
Exterior

Holiday Inn Express Boston - Waltham by IHG

Holiday Inn Express Boston - Waltham by IHG
2.5 star property
Piety Corner
9.0 out of 10, Wonderful, (1,001 reviews)
"Excellent property. Right next to the highway making it accessible for lots of locations by car, such as Salem, Maine, Vermont etc."
United Kingdom
christine
The price is CA $155
CA $173 total
includes taxes & fees
Jul 26 - Jul 27
Holiday Inn Express Boston - Waltham by IHG
Exterior

Best Western Plus Waltham Boston

Best Western Plus Waltham Boston
3.0 star property
Piety Corner
8.2 out of 10, Very good, (1,282 reviews)
"Good stay, calm, relax, good amenities and Breakfast."
United States
kiran
The price is CA $124
CA $138 total
includes taxes & fees
Aug 9 - Aug 10
Best Western Plus Waltham Boston
Exterior

Hampton Inn & Suites Watertown Boston

Hampton Inn & Suites Watertown Boston
2.5 star property
Watertown
9.4 out of 10, Exceptional, (1,091 reviews)
"The property was very clean, quiet, beds were comfortable, everything was updated & modern & the location was great."
United States
Jessica
The price is CA $218
CA $243 total
includes taxes & fees
Aug 16 - Aug 17
Hampton Inn & Suites Watertown Boston
Exterior

avid hotel Boston Logan Airport - Revere by IHG

avid hotel Boston Logan Airport - Revere by IHG
2.5 star property
Revere
9.0 out of 10, Wonderful, (1,599 reviews)
"Easy, clean Great place to stay for the night"
United States
Luanna
The price is CA $183
CA $205 total
includes taxes & fees
Aug 9 - Aug 10
avid hotel Boston Logan Airport - Revere by IHG
Exterior

Comfort Inn & Suites Logan International Airport

Comfort Inn & Suites Logan International Airport
2.5 star property
Revere
9.0 out of 10, Wonderful, (2,322 reviews)
"Great place to stay near the airport. airport shuttle was very convenient and great breakfast perfect place for a family"
United States
Emily
The price is CA $227
CA $262 total
includes taxes & fees
Aug 9 - Aug 10
Comfort Inn & Suites Logan International Airport
Front of property - evening/night

Porter Square Hotel

Porter Square Hotel
3.0 star property
North Cambridge
9.2 out of 10, Wonderful, (1,001 reviews)
"Great location, convenient valet parking. Rooms are small but nicely appointed and comfortable."
United States
Monique
The price is CA $224
CA $260 total
includes taxes & fees
Aug 2 - Aug 3
Porter Square Hotel
Exterior detail

Hotel 1868

Hotel 1868
3.5 star property
Agassiz
9.6 out of 10, Exceptional, (1,001 reviews)
"Great location. Friendly people."
United States
Todd
The price is CA $224
CA $260 total
includes taxes & fees
Aug 11 - Aug 12
Hotel 1868
Exterior

Holiday Inn Express Boston Logan Airport - Revere by IHG

Holiday Inn Express Boston Logan Airport - Revere by IHG
2.5 star property
Revere
9.2 out of 10, Wonderful, (1,348 reviews)
"Would stay again"
United States
Janice
The price is CA $193
CA $215 total
includes taxes & fees
Aug 2 - Aug 3
Holiday Inn Express Boston Logan Airport - Revere by IHG
View from room

Doubletree By Hilton Boston Logan Airport Chelsea

Doubletree By Hilton Boston Logan Airport Chelsea
4.0 star property
Chelsea
8.6 out of 10, Excellent, (1,854 reviews)
"Great location nice rooms"
United States
juan
The price is CA $206
CA $230 total
includes taxes & fees
Aug 9 - Aug 10
Doubletree By Hilton Boston Logan Airport Chelsea
Exterior

Hampton Inn Boston - Logan Airport

Hampton Inn Boston - Logan Airport
3.0 star property
Revere
8.2 out of 10, Very good, (5,550 reviews)
"Great place to stay, close to the airport."
United States
Scott
The price is CA $212
CA $237 total
includes taxes & fees
Aug 9 - Aug 10
Hampton Inn Boston - Logan Airport
Exterior

Cambria Hotel Boston Somerville

Cambria Hotel Boston Somerville
3.0 star property
Spring Hill
9.8 out of 10, Exceptional, (1,000 reviews)
"Excellent location, staff, and amenities on site. The restaurant in the hotel has convenient and great quality offerings. Would highly recommend this location."
United States
Amy
The price is CA $261
CA $292 total
includes taxes & fees
Aug 9 - Aug 10
Cambria Hotel Boston Somerville
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

The Midtown Hotel MOD Collection by Sonesta

The Midtown Hotel MOD Collection by Sonesta

10/10 Excellent
"The air conditioning system is very noisy."
Lynda 3-night trip
Posted 1 hour ago
The Midtown Hotel MOD Collection by Sonesta

Find out more about Winchester

Winchester Cabin Rentals information

Number of reviews
16,924
Accommodation
0 Cabin Rentals
Lowest Price
CA $138
Highest Price
CA $269

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 $269 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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