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The Little House. Historic 2-BR waterfront cottage in Winchester w/ WiFi, AC

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Exterior detail
Exterior detail
Room
Living area
Private kitchen

Reviews

10 out of 10
Exceptional
2 bedrooms1 bathroomSleeps 5

Popular amenities

  • Washer
  • Dryer
  • Air conditioning

Explore the area

View in a map
Winchester, MA
  • Place, Winter Pond
    ‪2 min walk‬
  • Place, Horn Pond
    ‪11 min walk‬
  • Place, Middlesex Fells Reservation
    ‪3 min drive‬
  • Airport, Bedford, MA (BED-Laurence G. Hanscom Field)
    ‪15 min drive‬

Rooms & beds

2 bedrooms (sleeps 5)

Bedroom 1

1 Queen Bed

Bedroom 2

2 Twin Beds

1 bathroom

Bathroom 1

Soap · Towels provided · Bathtub or shower · Bathtub · Toilet · Shampoo · Hair dryer

About this property

The Little House. Historic 2-BR waterfront cottage in Winchester w/ WiFi, AC

Your Winchester retreat awaits at this charming 2-bedroom cottage. Nestled in a tranquil setting, guests can unwind in the soothing ambiance of this terrific property. With a queen bed and a twin bed, this cozy space offers a comfortable stay for small groups. Complete with essential amenities like WiFi and a washing machine, this cottage provides everything you need for a relaxing getaway. Enjoy all that Winchester has to offer when you stay at our place.

Guests love how close the little house is to Boston and yet it feels like a lakefront vacation cottage. You'll love bird watching from the screen porch and from the bedrooms!
Our prices include all fees. No hidden fees.

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House Rules

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Children

Children allowed: ages 0-17
This house is not toddler proof - open staircase.
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Events

No events allowed
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Pets

No pets allowed
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Smoking

Smoking is not permitted

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property

About the neighborhood

Winchester

Winchester is home to this cottage. Tufts University and Fenway Park are notable landmarks, and the area's natural beauty can be seen at Boston Harbor and Boston Common. Consider Encore Boston Harbor for a night out, and don't miss New England Aquarium, a top local attraction.
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Map
Winchester, MA

What's nearby

  • Winter Pond - 2 min walk - 0.2 km
  • Horn Pond - 11 min walk - 1.0 km
  • Middlesex Fells Reservation - 3 min drive - 2.5 km
  • Harvard University - 13 min drive - 10.5 km
  • Fenway Park - 16 min drive - 16.5 km

Getting around

  • Winchester Station - 2 min drive
  • Medford / Tufts Station - 8 min drive
  • Bedford, MA (BED-Laurence G. Hanscom Field) - 25 min drive

Restaurants

  • ‪Sogno - ‬2 min drive
  • ‪Dunkin' - ‬2 min drive
  • ‪Dunkin' - ‬20 min walk
  • ‪Krave Kitchen & Bar - ‬19 min walk
  • ‪Black Horse Tavern - ‬3 min drive

Frequently asked questions

Is The Little House. Historic 2-BR waterfront cottage in Winchester w/ WiFi, AC pet-friendly?

No, pets are not allowed at this property.

How much does it cost to stay at The Little House. Historic 2-BR waterfront cottage in Winchester w/ WiFi, AC?

As of Apr 14, 2026, prices found for a 1-night stay for 2 adults at The Little House. Historic 2-BR waterfront cottage in Winchester w/ WiFi, AC on Apr 13, 2026 start from $250, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

Where is The Little House. Historic 2-BR waterfront cottage in Winchester w/ WiFi, AC located?

Situated in Winchester, this cottage is within 9 mi (15 km) of Tufts University, Harvard University, and Harvard Square. Encore Boston Harbor and Massachusetts Institute of Technology are also within 9 mi (15 km). Winchester Station is 21 minutes by foot and Winchester Wedgemere Station is 24 minutes.

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