Winchester Cottages

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Cottages in Winchester

WINTER 2025 PROMO -Lakefront 2 Bed / 3 bath + Extra Bed off of living room

Essex MA

This family-friendly cottage is 2.1 mi (3.4 km) from Essex River and 5.5 mi (8.9 km) from Long Hill.

Kitchen

Washer

Witchy Hideaway Cottage; Close to Beaches, Salem & Downtown Beverly

Beverly MA

$254 nightly

$283 total

Mar 19 - Mar 20

Total with taxes and fees

With a stay at this cottage in Beverly, you'll be within a 5-minute drive of Cabot Theater and John Cabot House.

Kitchen

Washer

Charming 1-bedroom seaside cottage in enchanting Marblehead with WiFi, AC

Marblehead MA

Located in Marblehead, this cottage is within a 5-minute drive of Marblehead Museum & Historical Society and Fort Sewall.

Washer

Dryer

5 Mi to TD Garden: Quiet Medford Getaway!

Medford MA

With a stay at this cottage in Medford, you'll be a 3-minute drive from Tufts University and 7 minutes from Encore Boston Harbor.

Kitchen

Parking included

Shore House Steps to the ocean, 18 min Ferry to Boston

Hull MA

When you stay at this cottage in Hull, you'll be by the sea and within a short 4-minute drive from Nantasket Beach.

Kitchen

Washer

Weymouth Waterfront Getaway w/ Swim Spa & Hot Tub

North Weymouth MA

With a stay at this cottage in North Weymouth, you'll be within a 15-minute drive of South Shore Plaza and South Shore Hospital.

Pool

Kitchen

Charming 2 Bedroom, 2 Bath, Coastal Carriage House in Marblehead

Marblehead MA

A stay at this cottage places you in the heart of Marblehead, within a 5-minute drive of Preston Beach and Marblehead Museum & Historical Society.

Kitchen

Washer

Charming 2-bedroom cottage in Westford, sandy beach, 2 pools, restaurant on site

Westford MA

With a stay at this cottage in Westford (Summer Village), you'll be a 4-minute drive from Stony Brook Conservation Land and 6 minutes from The Butterfly Place.

Pool

Hot Tub

Trail Access On-site: Gorgeous MCM Deck House!

Dover MA

Located in Dover, this cottage is within a 15-minute drive of Charles River Peninsula and Belkin Family Lookout Farm.

Kitchen

Washer

Clean Cottage w/Heated Pools - Hot Tub - Playground - Golf Cart: Family Retreat

Westford MA

With a stay at this cottage in Westford (Summer Village), you'll be a 4-minute drive from Stony Brook Conservation Land and 6 minutes from The Butterfly Place.

Pool

Hot Tub

Charming 2-bedroom Guest House in Dedham on Private Estate

Dedham MA

With a stay at this cottage in Dedham, you'll be within a 15-minute drive of Boston College and Legacy Place.

Washer

Dryer

Bright & Pet-friendly Home: 2 Mi to Harvard Square

Watertown MA

With a stay at this cottage in Watertown, you'll be within a 5-minute drive of Harvard University and Harvard Square.

Kitchen

Pet friendly

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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.