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Cottages in Middleton

Cozy Cottage Old Fashioned Charm
Enjoy a serene garden retreat with a patio, lush plants, and a wooden deck leading to the house.

Cozy Cottage Old Fashioned Charm

9.4 out of 10, Exceptional, (87)
"The cottage is cozy and quaint as described and includes all of the important necessities for an enjoyable stay. Janet and Mike are fabulous hosts--great communication, very kind and helpful!! Their number one goal as hosts is to have guests feel welcome and enjoy the beauty of Rockport and the surrounding areas :) Thank you Janet and Mike!! A++ rating :)"
Cozy Cottage Old Fashioned Charm
Charming 2 Bedroom, 2 Bath, Coastal Carriage House in Marblehead
Property grounds

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

Charming 2 Bedroom, 2 Bath, Coastal Carriage House in Marblehead
Glamorous Cabana: Poolside by day; Excellent Dining by night - perfect romantic getaway!
A heated pool

Glamorous Cabana: Poolside by day; Excellent Dining by night - perfect romantic getaway!

9.2 out of 10, Wonderful, (29)
"The trip was for my parent's 50th wedding anniversary. They said the place was wonderful and that they had an excellent time!"
$383 nightly
The price is $425
Aug 13 - Aug 14
Total includes taxes and fees
Glamorous Cabana: Poolside by day; Excellent Dining by night - perfect romantic getaway!
Charming cottage near the ocean w/beach access & near Gloucester
Fridge, microwave, oven, stovetop

Charming cottage near the ocean w/beach access & near Gloucester

7.6 out of 10, Good, (20)
"Beach cottage perfect for our needs. Great location, convenient to going everywhere including walking to the beach! Super easy check-in! Great rental."
Charming cottage near the ocean w/beach access & near Gloucester
Come home to Rockport!
Enjoy live performances and events in this grand hall with a stage and seating area.

Come home to Rockport!

10.0 out of 10, Exceptional, (110)
"Great place to stay, and plan to go again."
Come home to Rockport!
Cottage with Direct Water Access!
Enjoy a serene beach experience with calm waters and a wide expanse of sandy shore.

Cottage with Direct Water Access!

10.0 out of 10, Exceptional, (110)
"Perfect little cottage for my husband and I and our two dogs. Lots of day trips to see the sites and walk the dogs. Denise is a great host and easy to communicate with. Loved our stay, would definitely recommend!"
Cottage with Direct Water Access!
Luxury 1900's romantic retreat steps from the beach - King Suite!
Staircase leads to an upper level, flanked by pendant lights and a door to another room.

Luxury 1900's romantic retreat steps from the beach - King Suite!

9.8 out of 10, Exceptional, (45)
"much needed respite!"
Luxury 1900's romantic retreat steps from the beach - King Suite!
NEW -Lakefront 2 Bed / 3 bath + Extra Bed off of living room
Terrace/patio

NEW -Lakefront 2 Bed / 3 bath + Extra Bed off of living room

3.0 star property
10.0 out of 10, Exceptional, (11)
"We stayed at this lovely cottage on our trip to Salem,Ma and it is conveniently located within about 20 mins to Salem. While we were not visiting Salem we ventured around Gloucester and visited many delicious restaurants and viewed the ocean. 10/10 recommend and look forward to coming back!"
NEW -Lakefront 2 Bed / 3 bath + Extra Bed off of living room
Summer Cottage Fun! Minutes from the Beach
Walk along the designated beach pathway, marked by blue and white stripes, to the ocean's edge.

Summer Cottage Fun! Minutes from the Beach

10.0 out of 10, Exceptional, (3)
"Plum island is an amazing combination of beach fun and nature immersion. The cottage was cozy and more spacious than the pictures indicated, located a short walk away from two beach access points. The AC was also excellent, which isn’t always the case for beach rentals. This cottage is perfect for a relaxed vacation and I couldn’t recommend it enough. "
Summer Cottage Fun! Minutes from the Beach
Adorable Beach house with lots of outdoor space and steps to Long Beach!
Enjoy live performances and presentations in this elegant auditorium with a grand piano and ocean views.

Adorable Beach house with lots of outdoor space and steps to Long Beach!

10.0 out of 10, Exceptional, (22)
"Beautiful spot to enjoy a few days on the beach!"
Adorable Beach house with lots of outdoor space and steps to Long Beach!
Maids Quarters; private beach
Enjoy al fresco dining on the deck surrounded by lush greenery and trees.

Maids Quarters; private beach

2.0 star property
8.0 out of 10, Very Good, (2)
Maids Quarters; private beach
Good Harbor Beach House - walk to beach, close to restaurants and shopping!
Situated on a rocky shoreline, this historic building offers a picturesque setting with a sandy beach and calm waters.

Good Harbor Beach House - walk to beach, close to restaurants and shopping!

10.0 out of 10, Exceptional, (207)
"Property was just as described and pictured in online listing. It is a charming and cozy home with a beautiful view. It is conveniently located near Good Harbor Beach and downtown Gloucester. "
Good Harbor Beach House - walk to beach, close to restaurants and shopping!
Shore Cottage - Coastal gem, a traveler favorite! Outdoor patio, central AC.
Enjoy cooking in this well-equipped kitchen with a dishwasher, oven, microwave, and stove.

Shore Cottage - Coastal gem, a traveler favorite! Outdoor patio, central AC.

9.8 out of 10, Exceptional, (17)
"Even better in person, host had great hospitality, very clean, quiet, and lovely place to stay! We loved it!"
Shore Cottage - Coastal gem, a traveler favorite! Outdoor patio, central AC.
Big Fish, Little Pond. Fire Pit Swimming, Hiking, Kayaking, and Fishing!
Situated in a wooded area, this cabin features a front porch with a white picket fence and a gravel driveway leading to the entrance.

Big Fish, Little Pond. Fire Pit Swimming, Hiking, Kayaking, and Fishing!

9.2 out of 10, Wonderful, (11)
"A short walk to the lake where we enjoyed kayaking and were the first to use the new firepit. Great location with all the amenities you would need."
Big Fish, Little Pond. Fire Pit Swimming, Hiking, Kayaking, and Fishing!
Cozy oceanfront home with unique architecture
Relax in a serene oceanfront setting with lounge chairs and a shaded area amidst lush greenery.

Cozy oceanfront home with unique architecture

7.6 out of 10, Good, (39)
"The cottage is in a beautiful quiet location. The parking and walk to the cottage was as described. The views were incredible! Definitely will return next year"
Cozy oceanfront home with unique architecture
NEW 2BR Home Minutes to Downtown Rockport+Beach!
Enjoy a spacious interior with a sliding glass door leading to a furnished outdoor deck offering a view of the surrounding area.

NEW 2BR Home Minutes to Downtown Rockport+Beach!

9.8 out of 10, Exceptional, (9)
"Fantastic house for a family steps from the beach and stores!"
NEW 2BR Home Minutes to Downtown Rockport+Beach!
Beachfront 3 family home, best on the beach! Any a full week in summer add 250
Walk along the beachside boardwalk to the ocean's edge.

Beachfront 3 family home, best on the beach! Any a full week in summer add 250

9.8 out of 10, Exceptional, (12)
"We have been to Irish Mist many times..it is clean and inviting and a great place to enjoy family and the ocean.."
Beachfront 3 family home, best on the beach! Any a full week in summer add 250
Modern Cottage, Private Island, Unparalleled beauty
Enjoy cooking in this well-equipped kitchen with a spacious island and large windows offering a view of the outdoors.

Modern Cottage, Private Island, Unparalleled beauty

9.6 out of 10, Exceptional, (4)
"Loved the property. Very secluded and quiet. Nice place to stay if you’re going to Salem "
Modern Cottage, Private Island, Unparalleled beauty
5 Mi to TD Garden: Quiet Medford Getaway!
House (2 Bedrooms) | Interior

5 Mi to TD Garden: Quiet Medford Getaway!

3.0 star property
5 Mi to TD Garden: Quiet Medford Getaway!
Plum Island Beach Cottage - 4 Minute Walk To Beach!!
Stroll along the marina's covered walkway and enjoy the views of the boats docked below.

Plum Island Beach Cottage - 4 Minute Walk To Beach!!

2.0 star property
10.0 out of 10, Exceptional, (19)
"Place was in a great location. Short walk to the beach."
Plum Island Beach Cottage - 4 Minute Walk To Beach!!
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.
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Top Middleton Hotel Reviews

Hyatt Regency Boston/Cambridge

Hyatt Regency Boston/Cambridge

10/10 Excellent
"Great hotel, clean, spacious and nice area. Parking is pricey but its Boston. I would highly recommend the Hyatt Cambridge. I"
Michael 2-night trip
Posted 4 hours ago
Hyatt Regency Boston/Cambridge