Find Hotels with a Pool in Winchester, MA from CA $127

Start date: Check-in selected.
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check availability on Winchester Hotels with a Pool

Tonight
Sep 3 - Sep 4
Tomorrow
Sep 4 - Sep 5
This weekend
Sep 5 - Sep 7
Next weekend
Sep 12 - Sep 14

Top Winchester Hotels with a Pool

Our top choices for Winchester hotels with a pool

Seaport Hotel Boston
Indoor pool

Seaport Hotel Boston

4.0 star property
9.6 out of 10, Exceptional, (3351)
"Excellent hotel and location"
The price is CA $322
CA $382 total
includes taxes & fees
Sep 4 - Sep 5
Seaport Hotel Boston
Element Lexington
Indoor pool

Element Lexington

3.0 star property
8.4 out of 10, Very good, (1001)
"Great stay "
The price is CA $185
CA $206 total
includes taxes & fees
Sep 4 - Sep 5
Element Lexington
Hampton Inn & Suites Westford-Chelmsford
Indoor pool

Hampton Inn & Suites Westford-Chelmsford

2.5 star property
8.8 out of 10, Excellent, (1000)
"Great place!"
The price is CA $175
CA $195 total
includes taxes & fees
Sep 7 - Sep 8
Hampton Inn & Suites Westford-Chelmsford
Lakeside Inn
Seasonal outdoor pool

Lakeside Inn

2.0 star property
7.4 out of 10, Good, (2151)
"Clean rooms great parking. Great staff..fun little bar"
The price is CA $127
CA $142 total
includes taxes & fees
Sep 7 - Sep 8
Lakeside Inn
The Westin Boston Seaport District
Indoor pool

The Westin Boston Seaport District

4.0 star property
9.0 out of 10, Wonderful, (2154)
"Great place to stay"
The price is CA $284
CA $379 total
includes taxes & fees
Sep 21 - Sep 22
The Westin Boston Seaport District
Courtyard by Marriott Boston Waltham
Indoor pool

Courtyard by Marriott Boston Waltham

3.0 star property
9.2 out of 10, Wonderful, (1012)
"clean, friendly staff and convenient location to shops and site seeing. "
The price is CA $168
CA $188 total
includes taxes & fees
Sep 7 - Sep 8
Courtyard by Marriott Boston Waltham
DoubleTree by Hilton Boston North Shore
Indoor pool

DoubleTree by Hilton Boston North Shore

4.0 star property
8.0 out of 10, Very good, (2071)
"Very nice place to stay"
The price is CA $198
CA $221 total
includes taxes & fees
Sep 8 - Sep 9
DoubleTree by Hilton Boston North Shore
Aloft by Marriott, Boston Seaport District
Indoor pool

Aloft by Marriott, Boston Seaport District

3.0 star property
9.0 out of 10, Wonderful, (1346)
"We thoroughly enjoyed our stay! "
The price is CA $278
CA $364 total
includes taxes & fees
Sep 21 - Sep 22
Aloft by Marriott, Boston Seaport District
Homewood Suites by Hilton Boston Seaport District
Indoor pool

Homewood Suites by Hilton Boston Seaport District

3.0 star property
9.2 out of 10, Wonderful, (1255)
"Nice hotel with good service."
The price is CA $268
CA $308 total
includes taxes & fees
Sep 21 - Sep 22
Homewood Suites by Hilton Boston Seaport District
Sonesta Select Boston Danvers
Seasonal outdoor pool

Sonesta Select Boston Danvers

3.0 star property
8.6 out of 10, Excellent, (1015)
"Great stay! "
The price is CA $212
CA $237 total
includes taxes & fees
Sep 15 - Sep 16
Sonesta Select Boston Danvers
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.

Find out more about Winchester

Find out more about Winchester

Expand your search

Most booked related stays in Winchester in 2025

Hotels with pools in Winchester
Kid-friendly hotels
Kid-friendly hotels
Vacation rentals with pools in Winchester
Vacation homes with pools
Vacation homes with pools

Top Winchester Hotel Reviews

Hilton Boston Logan Airport

Hilton Boston Logan Airport

10/10 Excellent
"It was perfect to be close to the airport and a great shuttle"
johanna 1-night trip
Posted 4 days ago
Hilton Boston Logan Airport

Explore a world of travel with Expedia

Explore a world of travel with Expedia