Family-Friendly Vacation Rentals in Winchester Hospital, MA: Compare 10+ Sites & Save

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  2. Family Vacation Rentals
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  4.  Massachusetts

  5.  Boston
  6.  Winchester Hospital

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180 Best Family Vacation Rentals in Winchester Hospital (Starting from $58)

Modern Two Bedroom Condo - Boston
Modern Two Bedroom Condo - Boston
Apartment
Stoneham, MA, USA
2.0k from Winchester Hospital center

Apartments, Cheap, Accommodations, Parking, Lodgings, Vacation rentals, Beach, Places to stay, Family

2 Bedrooms6 Guests
8.0

Good

36 reviews

$288
Average price / night
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A charming modern suburban 3 bedroom condo close to Boston
A charming modern suburban 3 bedroom condo close to Boston
Condo
Stoneham, MA, 02180, United States
1.8k from Winchester Hospital center

AC, Balcony, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen

3 Bedrooms8 Guests
10.0

Exceptional

52 reviews

$494
Average price / night
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Modern Three Bedroom Condo - Boston
Modern Three Bedroom Condo - Boston
Apartment
Stoneham, MA, USA
2.0k from Winchester Hospital center

Apartments, Accommodations, Parking, Lodgings, Vacation rentals, Beach, Places to stay, Family, Self-catering

3 Bedrooms8 Guests
7.1

Good

37 reviews

$416
Average price / night
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Stylish Stoneham Getaway  Playground  Game Room
Stylish Stoneham Getaway Playground Game Room
House
Stoneham, MA, 02180, United States
3.2k from Winchester Hospital center

AC, Arcade, Balcony, Barbecue, Crib, Dryer, Free Parking, Heater, Internet

5 Bedrooms12 Guests
10.0

Exceptional

2 reviews

$1601
Average price / night
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Enchanting Hidden Door Escape
Enchanting Hidden Door Escape
House
MA, USA
2.3k from Winchester Hospital center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay

4 Bedrooms10 Guests
8.4

Very Good

5 reviews

$579
Average price / night
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Home in Woburn - Family + Pet Friendly!
Home in Woburn - Family + Pet Friendly!
House
Woburn, MA, 01801, United States
3.8k from Winchester Hospital center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

4 Bedrooms6 Guests
10.0

Exceptional

7 reviews

$377
Average price / night
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Up to 30% OFF 5BR Medford House, Free Parking, Close to Stone Zoo & Boston - 597
Up to 30% OFF 5BR Medford House, Free Parking, Close to Stone Zoo & Boston - 597
Apartment
Medford, MA, 02155, United States
4.0k from Winchester Hospital center

AC, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area, Microwave

5 Bedrooms6 Guests
8.4

Very Good

5 reviews

$428
Average price / night
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Your Cozy and Relaxing Retreat
Your Cozy and Relaxing Retreat
Apartment
Woburn, MA, USA
2.4k from Winchester Hospital center

Apartments, Cheap, Accommodations, Parking, Lodgings, Vacation rentals, Jacuzzis, Places to stay, Family

1 Bedroom2 Guests
10.0

Exceptional

2 reviews

$346
Average price / night
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The Niche: A cozy perfection!\nNewly Renovated Family Friendly! Near Boston
The Niche: A cozy perfection!\nNewly Renovated Family Friendly! Near Boston
House
Medford, MA, 02155, United States
4.0k from Winchester Hospital center

AC, Crib, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

3 Bedrooms8 Guests
10.0

Exceptional

8 reviews

$530
Average price / night
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5-bedroom house. Close to airport, bus & train. 10 min from Boston. Sleeps 10.
5-bedroom house. Close to airport, bus & train. 10 min from Boston. Sleeps 10.
House
Melrose, MA, 02176, United States
4.4k from Winchester Hospital center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

5 Bedrooms10 Guests
10.0

Exceptional

141 reviews

$500
Average price / night
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597 - 5BR Medford - Cozy Stay near Stone Zoo
597 - 5BR Medford - Cozy Stay near Stone Zoo
Apartment
Medford, MA, USA
4.0k from Winchester Hospital center

Apartments, Cheap, Accommodations, Parking, Pet-friendly, Lodgings, Places to stay, Family, Self-catering

5 Bedrooms6 Guests
10.0

Exceptional

3 reviews

$619
Average price / night
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Located north of Boston/ comfort and relaxation in your home away from home
Located north of Boston/ comfort and relaxation in your home away from home
House
Woburn, MA, 01801, United States
4.4k from Winchester Hospital center

AC, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking

1 Bedroom4 Guests
10.0

Exceptional

44 reviews

$398
Average price / night
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Cozy Medford Home Boston
Cozy Medford Home Boston
Apartment
Medford, MA, USA
4.4k from Winchester Hospital center

Internet, Parking, Air Conditioner, Security/Safety, Child Friendly

1 Bedroom7 Guests
New to Booking
$663
Average price / night
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Spacious 7-Room House Near Boston & Salem With Yard and Parking
Spacious 7-Room House Near Boston & Salem With Yard and Parking
House
Wakefield, MA, 01880, United States
4.6k from Winchester Hospital center

AC, Barbecue, Crib, Dryer, Fitness Equipment, Free Parking, Heater, Internet, Kitchen

3 Bedrooms11 Guests
10.0

Exceptional

14 reviews

$427
Average price / night
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Melrose 5-bedroom house
Melrose 5-bedroom house
House
Melrose, MA, USA
4.4k from Winchester Hospital center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay

5 Bedrooms10 Guests
10.0

Exceptional

1 reviews

$595
Average price / night
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Spacious & Convenient 1BR unit-20min to Boston
Spacious & Convenient 1BR unit-20min to Boston
House
Melrose, MA, 02176, United States
5.0k from Winchester Hospital center

AC, Crib, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

1 Bedroom4 Guests
9.8

Exceptional

15 reviews

$321
Average price / night
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Private Room in Melrose
Private Room in Melrose
House
Melrose, MA, USA
5.0k from Winchester Hospital center

Accommodations, Parking, Homestays, Lodgings, Places to stay

3 Bedrooms11 Guests
5.5

Review score

2 reviews

$58
Average price / night
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Super Family-Friendly! Spacious, cozy home base - close to Boston & Salem MA!
Super Family-Friendly! Spacious, cozy home base - close to Boston & Salem MA!
Apartment
Melrose, MA, 02176, United States
5.3k from Winchester Hospital center

AC, Arcade, Balcony, Crib, Free Parking, Heater, Internet, Kitchen, Living Area

2 Bedrooms5 Guests
10.0

Exceptional

70 reviews

$597
Average price / night
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Spacious and Cozy- near T-station-Quiet Neighborhood!
Spacious and Cozy- near T-station-Quiet Neighborhood!
Apartment
Malden, MA, USA
5.3k from Winchester Hospital center

Apartments, Cheap, Accommodations, Parking, Lodgings, Hot tubs, Places to stay, Self-catering

3 Bedrooms8 Guests
9.0

Fabulous

21 reviews

$270
Average price / night
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Luxury New House in Arlington with free parking
Luxury New House in Arlington with free parking
House
Arlington, MA, 02474, United States
5.4k from Winchester Hospital center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

9.4

Superb

3 reviews

$1218
Average price / night
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5 Mi to TD Garden Quiet Medford Getaway!
5 Mi to TD Garden Quiet Medford Getaway!
House
Medford, MA, USA
5.4k from Winchester Hospital center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay

2 Bedrooms5 Guests
8.0

Good

1 reviews

$289
Average price / night
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Charming 1-bedroom well located Garden Apartment in Historic West Medford
Charming 1-bedroom well located Garden Apartment in Historic West Medford
Apartment
Medford, MA, 02155, United States
5.4k from Winchester Hospital center

AC, Barbecue, Crib, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater, Internet

1 Bedroom4 Guests
New to Booking
$287
Average price / night
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6 Mi to Boston Common Apt in Medford!
6 Mi to Boston Common Apt in Medford!
Apartment
Medford, MA, USA
5.4k from Winchester Hospital center

Apartments, Accommodations, Parking, Lodgings, Places to stay

2 Bedrooms5 Guests
New to Booking
$261
Average price / night
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Modern 2BR/ Close to Boston with a lovely outdoor space
Modern 2BR/ Close to Boston with a lovely outdoor space
Apartment
Melrose, MA, 02176, United States
5.4k from Winchester Hospital center

AC, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area, Microwave

2 Bedrooms6 Guests
8.6

Fabulous

28 reviews

$325
Average price / night
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Lakeside Condo, 5min walk to charming small town and 20min train to Boston
Lakeside Condo, 5min walk to charming small town and 20min train to Boston
House
Wakefield, MA, 01880, United States
5.6k from Winchester Hospital center

AC, Barbecue, Dryer, Extra Bed, Fireplace, Fitness Equipment, Free Parking, Heater, Internet

1 Bedroom4 Guests
10.0

Exceptional

10 reviews

$148
Average price / night
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Entire near Boston Cottage House: MBTA, T, all major roads, parking
Entire near Boston Cottage House: MBTA, T, all major roads, parking
Cottage
Melrose, MA, 02176, United States
5.6k from Winchester Hospital center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

2 Bedrooms4 Guests
New to Booking
$336
Average price / night
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Funky and cozy home ! A little bit of everything for everyone.
Funky and cozy home ! A little bit of everything for everyone.
House
Arlington, MA, 02474, United States
5.8k from Winchester Hospital center

AC, Arcade, Barbecue, Crib, Dryer, Fitness Equipment, Free Parking, Heater, Internet

4 Bedrooms8 Guests
New to Booking
$494
Average price / night
Check Availability

Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Family Vacation Rentals in Winchester Hospital.

Where to stay in Winchester Hospital? Best neighborhoods & areas

Winchester Hospital Family Vacation Rentals on the Map

Frequently Asked Questions

You can explore 180 verified family-friendly vacation rentals in Winchester Hospital. These include spacious homes, villas, and condos designed to accommodate families of different sizes.

Prices for family-friendly rentals in Winchester Hospital vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $58 per night, with larger homes and peak travel periods often costing more.

Many family-friendly rentals in Winchester Hospital offer baby-friendly items such as high chairs, cribs, or pack-and-play options. Availability can vary, so it’s helpful to check the listing details before booking.

Yes, some rentals in Winchester Hospital are well suited for multi-generational stays, offering multiple bedrooms, separate living areas, and enough space for larger groups to stay comfortably together.

For busy travel periods such as school holidays or summer breaks, booking 90 to 120 days in advance is recommended to secure the best options. Availability may be more flexible during quieter times of the year.

Family-friendly rentals in Winchester Hospital often include amenities such as Child Friendly, Fireplace/Heating, and Internet. These features help make stays more convenient and enjoyable for both adults and children.

You can use search filters to find rentals that offer features like game rooms, playgrounds, or entertainment areas. Checking property descriptions can also help you identify homes that are well suited for families with children.