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The 10 Best Massachusetts Cottages – Vacation Cottages in Massachusetts, United States of America

Check out our selection of great cottages in Massachusetts

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Review Score

Wonderful: 9+ Very Good: 8+ Good: 7+ Pleasant: 6+
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Inkwell Beach Cottage

Oak Bluffs

This oceanfront bed and breakfast in Martha’s Vineyard is just 5 minutes’ walk from the ferry and features free Wi-Fi and full daily breakfast. The Niantic Park Tennis Courts are 10 minutes’ walk.

Admire the ocean views on the large front terrace at Isabelle’s Beach House B&B. Relax in the common living area or read a complimentary newspaper by the fireplace. Host was exceptional! Good breakfast each day! Location close to everything! Place was very clean!

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9.1
Wonderful
140 reviews
Price from
$281.75
per night

Indian Lake House

Worcester

Boasting air-conditioned accommodation with a balcony, Indian Lake House is situated in Worcester. Guests can benefit from a patio and an outdoor fireplace. The villa also features free WiFi, free private parking and facilities for disabled guests. The view of the lake from the porch and the kitchen amenities.

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9
Wonderful
7 reviews
Price from
$198
per night

Renovated & Sophisticated Home Near Beach & Shops!

Barnstable

Featuring a spa bath, Renovated & Sophisticated Home Near Beach & Shops! is located in Barnstable. This property offers access to a terrace, free private parking and free WiFi. The property is non-smoking and is situated 23 km from Sandwich Glass Museum. Our stay was incredible. The host was very friendly and accommodating, making our stay extra special. The house was well located and clean, offering all the amenities needed on a daily basis. We'll definitely be back.

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9.8
Exceptional
5 reviews
Price from
$450
per night

Island Time

Vineyard Haven

Island Time, boasting a garden, is located in Vineyard Haven, 1.9 km from Eastville Beach and 13 km from Edgartown Lighthouse. It is situated 1.3 km from Tisbury Town Beach and features an ATM. Free WiFi is available throughout the property and Owen Park Beach is 500 metres away. Great location and a very nice well equipped apartment

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9.6
Exceptional
5 reviews
Price from
$206
per night

Woodland Hills Modern Cottage Minutes from Downtown Great Barrington

Great Barrington

Boasting a spa bath, Woodland Hills Modern Cottage Minutes from Downtown Great Barrington is set in Great Barrington. The property has garden and quiet street views, and is 11 km from Norman Rockwell Museum. There is a sun terrace and guests can make use of free WiFi and free private parking. Great house! Very nicely decorated house with lots of space. The kitchen is beautiful and well-equipped. with plenty of information on how to use the amenities and where to dine, etc. In general, Rob, the owner, was extremely attentive. He even accepted a medical device delivery for my mother a day before our arrival. Great Barrington is my favorite town in the Berkshires, and Rob's house is situated in the perfect spot. It is perfectly nestled in a nice neighborhood that "feels" far from the downtown area, since it's surrounded by the woods, but it's actually only a few minutes away. My favorite part of the house is the coffee bar! I will definitely stay here again on my next trip to the Berkshires.

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9.6
Exceptional
5 reviews
Price from
$450
per night

Sea House

Chatham

Sea House is set in Chatham, 2.4 km from Chatham Lighthouse Beach, 26 km from Nauset Lighthouse, and 36 km from Wellfleet Bay Wildlife Sanctuary. This holiday home is 38 km from Cape Cod National Seashore and 49 km from Truro Historical Museum. Free WiFi is available throughout the property and Oyster Pond Beach is 1.3 km away. Loved the house and the location was amazing.

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9.7
Exceptional
7 reviews
Price from
$174
per night

Sandbars Inn - Beachside Cottage

North Truro

Situated in North Truro, just 60 metres from Beach Point, Sandbars Inn - Beachside Cottage features beachfront accommodation with free WiFi. The air-conditioned accommodation is 2.8 km from Noons Landing. The property is non-smoking and is set 3.4 km from Commercial Street. Twin beds were perfect for the kids. Close to Provincetown for food and Cape Cod National Seashore.

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9.6
Exceptional
5 reviews

The Lemonade Stand

West Tisbury

Set in West Tisbury in the Massachusetts region, The Lemonade Stand has a patio. Free WiFi is available throughout the property and Edgartown Lighthouse is 11 km away.

The air-conditioned holiday home consists of 1 bedroom, a living room, a fully equipped kitchen with a dishwasher and a coffee machine, and 1 bathroom with a bath and a hair dryer. Towels and bed linen are offered in the holiday home. The property has an outdoor dining area. The Lemonade Stand was beautiful. The property was tucked away in a magical forest and was perfect for us and the dogs. The house was very unique and we just loved our stay. Highly recommend and we would love to come back. Thank you.

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9.2
Wonderful
5 reviews
Price from
$266
per night

2 Minute Walk to Beach, Cape Cod Escape

Dennis Port

Set in Dennis Port in the Massachusetts region, 2 Minute Walk to Beach, Cape Cod Escape features a patio. The air-conditioned accommodation is 400 metres from Sea Street Beach, and guests can benefit from private parking available on site and free WiFi. The property is non-smoking and is located 1.5 km from South Village Beach. Everything was great and it was our second stay at this location.

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9.8
Exceptional
9 reviews
Price from
$135
per night

1 bed cottage, water views & water access

Handy Four Corners

Located in Handy Four Corners, 43 km from International Tennis Hall of Fame and 44 km from Rosecliff Mansion, 1 bed cottage, water views & water access offers a private beach area and air conditioning. This property offers access to a balcony, free private parking and free WiFi. The property is non-smoking and is set 45 km from The Preservation Society of Newport County. Nice, peaceful location, about 10 minute drive to Horseneck Beach. Large living room/kitchen and large bedroom, with beautiful views. Large TV and good Wi-Fi. Easy parking on private driveway. Very friendly hosts, living in main house adjacent. Would definitely stay here again!

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9.2
Wonderful
19 reviews
Price from
$209.30
per night

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