Winchester Town Hall and First Congregational Church at Winchester Center Historic District panorama in downtown Winchester, Massachusetts, USA.

Winchester Vacation Rentals

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Check prices for these dates

In two weeks
Jul 3 - Jul 5
In two months
Aug 14 - Aug 16
In three months
Sep 11 - Sep 13
In four months
Oct 9 - Oct 11

Our top choices for Winchester vacation rentals

1 Queen Bed with Sofa Bed (6th Floor - Elevator stops on 5th then stairs up) | Desk, iron/ironing board, free WiFi, bed sheets

Temple Place Suites

Temple Place Suites
2.5 star property
Downtown Boston
7.0 out of 10, Good, (390 reviews)
"Wonderful stay at this property. Location was excellent, and the host is very quick and responsive to answer any questions you may have."
United States
Jennifer
The price is ￥19,325
￥32,343 total
includes taxes & fees
Jun 17 - Jun 18
Temple Place Suites
Premium Apartment | Living area | 24-inch Smart TV with digital channels

The Chester Hotel

The Chester Hotel
4.0 star property
South End
8.6 out of 10, Excellent, (33 reviews)
"Charming room, fresh towels, clean!! I would stay here again."
United States
Mary
The price is ￥25,638
￥49,732 total
includes taxes & fees
Jun 30 - Jul 1
The Chester Hotel
Deluxe Double Room, Shared Bathroom | Iron/ironing board, free WiFi, bed sheets

Premier Suites - Bay Village

Premier Suites - Bay Village
2.0 star property
Bay Village
6.2 out of 10, (291 reviews)
"Great location and well maintained"
United States
EDDIE
The price is ￥19,325
￥30,503 total
includes taxes & fees
Jun 17 - Jun 18
Premier Suites - Bay Village
Interior

Enjoyable 2-bedroom lower level apartment in charming Lynn

Enjoyable 2-bedroom lower level apartment in charming Lynn
Lynn
9.6 out of 10, Exceptional, (10 reviews)
The price is ￥23,555
￥42,715 total
includes taxes & fees
Jul 7 - Jul 8
Enjoyable 2-bedroom lower level apartment in charming Lynn
Suite (Luxury 1BR w/ King Bed & City Views) | Egyptian cotton sheets, premium bedding, down comforters

Symple Live

Symple Live
4.5 star property
Fenway–Kenmore
8.0 out of 10, Very Good, (2 reviews)
"The property was great, aside from very busy outside streets, which made it difficult to sleep, but was not the fault of the host."
United States
Nicholas
The price is ￥27,719
￥47,518 total
includes taxes & fees
Jul 15 - Jul 16
Symple Live
Marina

♥ Historic Studio Minutes to Salem+Beaches Old Town Marblehead Private Parking ♥

♥ Historic Studio Minutes to Salem+Beaches Old Town Marblehead Private Parking ♥
Marblehead Historic District
9.8 out of 10, Exceptional, (74 reviews)
"Great location, clean and comfortable, responsive host. Overall, a terrific stay. "
United States
Tiffany F.
The price is ￥18,085
￥45,079 total
includes taxes & fees
Jun 16 - Jun 17
♥ Historic Studio Minutes to Salem+Beaches Old Town Marblehead Private Parking ♥
Outdoor dining

🎖The Boiler Room - Close to Subway & Downtown🎖

🎖The Boiler Room - Close to Subway & Downtown🎖
Dorchester
9.8 out of 10, Exceptional, (81 reviews)
"Host was amazing and responded right away with any questions or concerns we had! Beautiful place to stay!"
United States
Amy I.
The price is ￥23,876
￥65,022 total
includes taxes & fees
Jun 21 - Jun 22
🎖The Boiler Room - Close to Subway & Downtown🎖
Exterior

Light-filled Studio | Back Bay

Light-filled Studio | Back Bay
Back Bay
10.0 out of 10, Exceptional, (2 reviews)
"It was a great stay!"
United States
Adina S.
The price is ￥13,140
￥40,700 total
includes taxes & fees
Jul 6 - Jul 7
Light-filled Studio | Back Bay
Terrace/patio

Gorgeous Beacon Hills Studio next to State house

Gorgeous Beacon Hills Studio next to State house
Beacon Hill
9.8 out of 10, Exceptional, (33 reviews)
"We had a great stay and host was welcoming and responsive. Thanks!"
United States
Eric M.
The price is ￥33,490
￥62,995 total
includes taxes & fees
Jun 30 - Jul 1
Gorgeous Beacon Hills Studio next to State house
1 bedroom, WiFi

Modern North End Studio

Modern North End Studio
North End
9.4 out of 10, Exceptional, (17 reviews)
"Lovely flat in fantastic location."
United States
James
Modern North End Studio
Lobby lounge

Global Luxury Suites Downtown Boston

Global Luxury Suites Downtown Boston
4.0 star property
Chinatown
8.0 out of 10, Very Good, (706 reviews)
"Clean room, great staff and fantastic location for a reasonable price."
United States
April
The price is ￥24,402
￥46,470 total
includes taxes & fees
Jul 6 - Jul 7
Global Luxury Suites Downtown Boston
Smart TV, fireplace

Private Cozy 1-br condo w/ high ceilings, WiFi, AC in quiet N. Framingham

Private Cozy 1-br condo w/ high ceilings, WiFi, AC in quiet N. Framingham
Framingham
10.0 out of 10, Exceptional, (5 reviews)
"Very nice and private. Reasonably close to commuter lines into Boston."
United States
Jenny S.
The price is ￥21,472
￥34,902 total
includes taxes & fees
Jun 23 - Jun 24
Private Cozy 1-br condo w/ high ceilings, WiFi, AC in quiet N. Framingham
1 bedroom, desk, iron/ironing board, WiFi

Studio Awaits Your Next Stay!

Studio Awaits Your Next Stay!
Bay Village
8.4 out of 10, Very Good, (6 reviews)
"Would stay again"
United States
mark p.
The price is ￥24,356
￥45,170 total
includes taxes & fees
Jun 21 - Jun 22
Studio Awaits Your Next Stay!
TV

Beautiful 1BR near Fenway Park + Kenmore!

Beautiful 1BR near Fenway Park + Kenmore!
Fenway–Kenmore
The price is ￥22,914
￥58,672 total
includes taxes & fees
Jun 21 - Jun 22
Beautiful 1BR near Fenway Park + Kenmore!
Fridge, microwave, oven, stovetop

2BR Historic Marblehead Home+Minutes to Beach

2BR Historic Marblehead Home+Minutes to Beach
Marblehead Historic District
10.0 out of 10, Exceptional, (23 reviews)
"This is a lovely house, perfect for people who need two bedrooms but can share a bathroom. The location is great. Parking was not a problem during our stay in early June. We walked in the neighborhood each day to admire the houses and gardens. People were friendly and we visited with a few dogs. The kitchen is modern. The fridge was 100% empty, so bring or shop for everything you need including butter, condiments, salad dressing etc. The air conditioners worked well. We didn’t have a way to...
United States
Shanti
The price is ￥25,392
￥68,815 total
includes taxes & fees
Jul 7 - Jul 8
2BR Historic Marblehead Home+Minutes to Beach
Exterior detail

Charming 1-bedroom condo in marvelous Marblehead with hidden patio

Charming 1-bedroom condo in marvelous Marblehead with hidden patio
Marblehead Historic District
10.0 out of 10, Exceptional, (6 reviews)
"Darling apartment - perfectly located close to shops and restaurants in downtown Marblehead. "
United States
Lauren P.
The price is ￥21,632
￥45,104 total
includes taxes & fees
Jun 16 - Jun 17
Charming 1-bedroom condo in marvelous Marblehead with hidden patio
Interior

Perfetto North End 1brm

Perfetto North End 1brm
North End
9.8 out of 10, Exceptional, (15 reviews)
"Great location- excellent place!"
United States
Deborah S.
Perfetto North End 1brm
Marina

Cozy Seaside studio in charming Marblehead with AC, WiFi. Short walk to downtown

Cozy Seaside studio in charming Marblehead with AC, WiFi. Short walk to downtown
Marblehead
10.0 out of 10, Exceptional, (26 reviews)
"Absolutely beautiful little place within walking distance of the beach and only a short drive to stores. "
United States
Patricia
The price is ￥28,843
￥53,337 total
includes taxes & fees
Jun 17 - Jun 18
Cozy Seaside studio in charming Marblehead with AC, WiFi. Short walk to downtown
Shower, hair dryer

Central Salem Retreat 2bd W/ parking

Central Salem Retreat 2bd W/ parking
Salem
9.2 out of 10, Wonderful, (15 reviews)
"It was very clean, a great location, and the host was super responsive and helpful!"
United States
Kristen N.
The price is ￥15,864
￥36,918 total
includes taxes & fees
Jun 16 - Jun 17
Central Salem Retreat 2bd W/ parking
Smart TV

Artful Escape • Minutes to Salem, Beach and Train to Boston • Private Parking

Artful Escape • Minutes to Salem, Beach and Train to Boston • Private Parking
Beverly
9.2 out of 10, Wonderful, (25 reviews)
"Cheerful decor, well-equipped kitchen, and clean. Good location in walking distance to restaurants. However, there was a musty smell throughout the building and rooms. "
United States
Julia
The price is ￥21,738
￥58,290 total
includes taxes & fees
Jun 17 - Jun 18
Artful Escape • Minutes to Salem, Beach and Train to Boston • Private Parking
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

Omni Parker House

Omni Parker House

10/10 Excellent
"Great location and helpful staff"
Calum 4-night trip
Posted less than an hour ago
Omni Parker House

Find out more about Winchester

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Frequently asked questions

Can I find vacation rentals in Winchester?

Yes, we have vacation rentals in Winchester close to Winter Pond, or you can choose a more remote option if you're looking for a relaxing stay. Winchester is known for its soccer matches and lake views.

What are some of the best vacation home rentals in Winchester?

Cozy 3BD 1BA near Beach T-10 Min from Boston: This vacation home rental outside of Winchester is equipped with a patio, free WiFi, and a Smart TV to help you feel comfortable during your stay. It has 3 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family.

What can I see and do in Winchester?

While exploring the area, visit family-friendly sights like Winter Pond, or get outside and enjoy nature at Boston Harbor. Fenway Park and Encore Boston Harbor are other popular places to visit in the area.

What are vacation rentals like in Winchester?

Vacation rentals are privately owned properties you can book for a few days or a quick weekend in Winchester. Vacation rentals feature extras like laundry facilities and kitchens so you'll feel right at home. If you're concerned about a sanitized environment, vacation rentals can offer a sense of seclusion away from shared hotel elevators and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular option for a family trip.