Winthrop Cottages

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Cottages in Winthrop

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 2.1 mi (3.4 km) from Essex Shipbuilding Museum.

Kitchen

Washer

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

Beverly MA

$213 nightly

$238 total

Mar 5 - Mar 6

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.

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.

Summer Sea Cottage -On Scituate Harbor

Scituate MA

With a stay at this cottage in Scituate, you'll be within a 10-minute walk of Massachusetts Bay and Museum Beach.

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.

Cozy Pet Friendly House Next To Train

Canton MA

With a stay at this cottage in Canton, you'll be within a 15-minute drive of Gillette Stadium and Brookmeadow Country Club.

Washer

Dryer

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

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.

16 Mi to Boston: Home w/ Deck in Weymouth

South Weymouth MA

With a stay at this cottage in South Weymouth, you'll be within a 5-minute drive of South Shore Hospital and Union Point Dog Park.

Kitchen

Washer

Escape to Cape Ann Steps to Beach & Pier!

Gloucester MA

With a stay at this cottage in Gloucester (Magnolia), you'll be within a 5-minute drive of Coolidge Reservation and Black Beach.

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.

Unique Scituate Vacation Rental on Herring River!

Scituate MA

With a stay at this cottage in Scituate, you'll be within a 5-minute drive of Stockbridge Grist Mill and North River Wildlife Sanctuary.

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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.