Vacation Rentals in Winchester, MA

PRICE PER NIGHT

ACCOMMODATION TYPES

Sleep up to 4 Guest New Apt. 10 mins to Boston Easy to I-93
6.7

Good

·
Winchester Highlands
·
1 br
·
Sleeps 4
·
Air Conditioning · Fitness Center · Dishwasher ·
From
$120/night
Check availability
Property
Apartment · 1 Bed · 1 bath
Amenities
Air Conditioning
Fitness Center
Dishwasher
Furnished
Ski In Ski Out
In Unit Laundry
Wifi
Oven
Other spaces
Kitchen, Workspace
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Spacious Apartment - 5 miles from Boston!

No reviews

·
Glenwood
·
4 br
·
Sleeps 4
·
In Unit Laundry · Furnished · Kitchen ·
From
$198/night
Check availability
Property
Apartment · 4 Beds · 2 baths
Amenities
In Unit Laundry
Furnished
Other spaces
Kitchen
Boston area house & gardens, near parks, farms, woods trails, shops, buses

No reviews

·
Arlington Heights
·
4 br
·
Sleeps 9
·
On Site Laundry · Hardwood Floor · Air Conditioning ·
From
$150/night
Check availability
Property
House · 4 Beds · 2 baths
Amenities
On Site Laundry
Hardwood Floor
Air Conditioning
Dishwasher
Furnished
In Unit Laundry
Wifi
Oven
Other spaces
Kitchen
New Single Family 5b/3b with Central AC
9.6

Excellent

·
Arlington Heights
·
5 br
·
Sleeps 12
·
Outdoor Space · Fireplace · Air Conditioning ·
From
$638/night
Check availability
Property
House · 5 Beds · 3 baths
Amenities
Fireplace
Air Conditioning
Dishwasher
Furnished
In Unit Laundry
Wifi
Oven
Garage Parking
Other spaces
Kitchen, Workspace
Family-friendly House in Quiet Neighborhood, 5 miles away from Boston!

No reviews

·
North Medford
·
4 br
·
Sleeps 5
·
In Unit Laundry · Kitchen · Furnished ·
From
$399/night
Check availability
Property
House · 4 Beds · 2 baths
Amenities
In Unit Laundry
Furnished
Dishwasher
Other spaces
Kitchen
Brand New 4 Bedroom Colonial
10

Excellent

·
Downtown Woburn
·
4 br
·
Sleeps 6
·
Pool · Fireplace · Private Pool ·
From
$198/night
Check availability
Property
House · 4 Beds · 3 baths
Amenities
Pool
Fireplace
Private Pool
Air Conditioning
Dishwasher
Furnished
In Unit Laundry
Wifi
Other spaces
Kitchen, Workspace
One bedroom located on quiet street close to highway

No reviews

·
Lawrence Estates
·
1 br
·
Sleeps 1
·
In Unit Laundry · Air Conditioning · Furnished ·
From
$100/night
Check availability
Property
House · 1 Bed · 2 baths
Amenities
In Unit Laundry
Air Conditioning
Furnished
Wifi
5 Star Immaculate Home 15 miles from Boston. Sleeps 4

No reviews

·
Cummingsville
·
2 br
·
Sleeps 3
·
Outdoor Space · Beach · Air Conditioning ·
From
$369/night
Check availability
Property
House · 2 Beds · 3 baths
Amenities
Beach
Air Conditioning
Dishwasher
Furnished
In Unit Laundry
Wifi
Oven
Other spaces
Kitchen
Room B , 15 min drive to Harvard
8

Very good

·
Edgeworth
·
1 br
·
Sleeps 1
·
Furnished ·
From
$78/night
Check availability
Property
House · 1 Bed · 1 bath
Amenities
Furnished

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Beautiful Two Bedroom Condo Near Boston
10

Excellent

·
Stoneham
·
2 br
·
Sleeps 6
·
On Site Laundry · Air Conditioning · Fitness Center ·
From
$119/night
Check availability
Property
Condo · 2 Beds · 1 bath
Amenities
On Site Laundry
Air Conditioning
Fitness Center
Dishwasher
Furnished
In Unit Laundry
Wifi
Oven
Other spaces
Kitchen
Modern Three Bedroom Condo - Near Boston
10

Excellent

·
Stoneham
·
3 br
·
Sleeps 8
·
On Site Laundry · Balcony · Beach ·
From
$143/night
Check availability
Property
Condo · 3 Beds · 1 bath
Amenities
On Site Laundry
Beach
Lake
Waterfront
Air Conditioning
Dishwasher
Furnished
In Unit Laundry
Other spaces
Balcony, Kitchen, Workspace
Cheerful New Townhouse
10

Excellent

·
Glenwood
·
4 br
·
Sleeps 8
·
On Site Laundry · Air Conditioning · Fitness Center ·
From
$695/night
Check availability
Property
House · 4 Beds · 3 baths
Amenities
On Site Laundry
Air Conditioning
Fitness Center
Dishwasher
Furnished
In Unit Laundry
Wifi
Oven
Other spaces
Kitchen, Workspace
Unique Cathedral Ceiling Condo W/D, Parking

No reviews

·
Arlington Heights
·
2 br
·
Sleeps 6
·
On Site Laundry · Assigned Parking · Air Conditioning ·
From
$225/night
Check availability
Property
House · 2 Beds · 1 bath
Amenities
On Site Laundry
Assigned Parking
Air Conditioning
Dishwasher
Furnished
In Unit Laundry
Wifi
Oven
Other spaces
Kitchen, Workspace
Deluxe and Bright 3Br, King Bed,W/D,Parking

No reviews

·
Arlington Heights
·
3 br
·
Sleeps 6
·
Assigned Parking · Air Conditioning · Dishwasher ·
From
$280/night
Check availability
Property
Condo · 3 Beds · 1 bath
Amenities
Assigned Parking
Air Conditioning
Dishwasher
Furnished
In Unit Laundry
Wifi
Oven
Garage Parking
Other spaces
Kitchen, Workspace
Stylish Studio - ✓Sanitized ✓Private ✓Spotless

No reviews

·
Arlington Heights
·
1 br
·
Sleeps 4
·
Air Conditioning · Furnished · In Unit Laundry ·
From
$120/night
Check availability
Property
Apartment · 1 Bed · 1 bath
Amenities
Air Conditioning
Furnished
In Unit Laundry
Wifi
Other spaces
Kitchen, Workspace
★Modern Studio-Private Entrance,Washer+Dryer★

No reviews

·
Arlington Heights
·
1 br
·
Air Conditioning · Furnished · In Unit Laundry ·
From
$120/night
Check availability
Property
Apartment · 1 Bed · 1 bath
Amenities
Air Conditioning
Furnished
In Unit Laundry
Wifi
Other spaces
Kitchen, Workspace
Perfect Stoneham Getaway Just Minutes to Boston!

No reviews

·
Stoneham
·
2 br
·
Sleeps 6
·
Outdoor Space · Air Conditioning · Dishwasher ·
From
$203/night
Check availability
Property
House · 2 Beds · 1 bath
Amenities
Air Conditioning
Dishwasher
Furnished
In Unit Laundry
Wifi
Oven
Garage Parking
Other spaces
Kitchen
NEW Lovely Studio Apt. Near both forest reservoir & Downtown
10

Excellent

·
Lawrence Estates
·
1 br
·
Sleeps 4
·
Air Conditioning · Fitness Center · Furnished ·
From
$155/night
Check availability
Property
Apartment · 1 Bed · 1 bath
Amenities
Air Conditioning
Fitness Center
Furnished
In Unit Laundry
Wifi
Oven
Free Parking
Other spaces
Kitchen
Beautiful 2beds/1bath w/free parking & 10mnts away from Boston
10

Excellent

·
Glenwood
·
2 br
·
Sleeps 5
·
Air Conditioning · Dishwasher · Furnished ·
From
$198/night
Check availability
Property
Condo · 2 Beds · 1 bath
Amenities
Air Conditioning
Dishwasher
Furnished
Wifi
Oven
Other spaces
Kitchen, Workspace
Beautifully furnished 3 bedrooms close to Boston Apt up to 5 adults
9.5

Excellent

·
Oak Grove
·
3 br
·
Sleeps 5
·
Beach · Lake · Waterfront ·
From
$350/night
Check availability
Property
House · 3 Beds · 1 bath
Amenities
Beach
Lake
Waterfront
Ocean
Dishwasher
Furnished
In Unit Laundry
Wifi
Other spaces
Kitchen
Charming Colonial Two Bedroom Basement Apartment
10

Excellent

·
Glenwood
·
2 br
·
Sleeps 5
·
Air Conditioning · Dishwasher · Furnished ·
From
$157/night
Check availability
Property
House · 2 Beds · 1 bath
Amenities
Air Conditioning
Dishwasher
Furnished
In Unit Laundry
Wifi
Oven
Other spaces
Kitchen, Workspace
Located north of Boston/ comfort and relaxation in your home away from home
9.8

Excellent

·
Cummingsville
·
1 br
·
Sleeps 4
·
Outdoor Space · Walk In Closets · Air Conditioning ·
From
$131/night
Check availability
Property
House · 1 Bed · 1 bath
Amenities
Walk In Closets
Air Conditioning
Dishwasher
Furnished
In Unit Laundry
Wifi
Oven
Other spaces
Kitchen
Quiet and spacious 2 floor-3 bedroom condo
10

Excellent

·
Oak Grove
·
3 br
·
Sleeps 6
·
Balcony · Air Conditioning · Furnished ·
From
$375/night
Check availability
Property
Condo · 3 Beds · 1 bath
Amenities
Air Conditioning
Furnished
In Unit Laundry
Wifi
Oven
Other spaces
Balcony, Kitchen, Workspace
Beautiful renovated 3 bedroom apt near Boston.
9.9

Excellent

·
Glenwood
·
3 br
·
Sleeps 7
·
Air Conditioning · Dishwasher · Furnished ·
From
$200/night
Check availability
Property
House · 3 Beds · 1 bath
Amenities
Air Conditioning
Dishwasher
Furnished
In Unit Laundry
Wifi
Oven
Other spaces
Kitchen
Home > Massachusetts Vacation Rentals > Winchester Vacation Rentals
Updated: March 27, 2023

Learn about vacation rentals in

Winchester

Explore 1 vacation rentals near Winchester, Massachusetts. Whether you’re a tourist or on a staycation, there’s plenty of things to do and restaurants to try around the city. If you’re looking to take a trip to Winchester, you can see photos of Winchester vacation rentals, view amenities and features, browse by specific property types, and more. Use our interactive map to find Winchester vacation rentals in specific areas. Whether you’re looking for a Winchester staycation, weekend getaway, or a long vacation, we’ve got you covered. Use the date filters at the top to select your travel dates and view availability. The lowest vacation rental price in Winchester is $120 per night and the highest price is $120 per night.
The most common amenities for vacation rentals near Winchester are: fitness center, garage parking, and dishwasher. To find vacation properties that might be a good option for large groups or families, use our filters for bedroom count, bathroom count and more.

1 bed rentals

1 available

Vacation Rentals in Winchester, MA FAQ

How many vacation rentals in Winchester are available?

There are currently 1 vacation rentals in Winchester available. Our vacation rentals in Winchester include nightly rentals, weekend rentals, weekly rentals, and monthly rentals.

Are there any pet friendly vacation rentals in Winchester?

No, right now there are no pet friendly vacation rentals in Winchester. A pet friendly vacation rental in Winchester means a rental home that is dog friendly or cat friendly. Some pet friendly homes may accommodate other types of pets, as well. Contact the listing agent for any pet related inquiries.

Are there any vacation rentals in Winchester with a pool?

No there are no vacation rentals with a pool available in Winchester, MA. View more detailed vacation spots on Vacations by Zumper.

Are there any vacation rentals in Winchester with internet access?

As of March 27, 2023, there are vacation rentals with internet access available in Winchester, Massachusetts. Check out more enjoyable destinations on Vacations by Zumper.

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