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Compare 57 Cottages in Middleton with updated reviews, rates, and availability.

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

9.6 out of 10, Exceptional, (34)
"We had a wonderful stay at this darling cottage. The kitchen was completely stocked with everything you can imagine you would need. Bed was comfortable. There was a neighborhood turkey that was very entertaining. Thank you."
Luxury 1900's romantic retreat steps from the beach - King Suite!

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

10.0 out of 10, Exceptional, (195)
"This house served as a lovely place for our family to gather for a christmas dinner. The house had good amenities. Everyone loved the location and distance to nearby Good Harbor beach was a plus even in the winter cold. local road needs work, cars all bottomed out on the road. Thank you for hospitality. "
Good Harbor Beach House - walk to beach, close to restaurants and shopping!

Cottage with Direct Water Access!

10.0 out of 10, Exceptional, (108)
"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!

Coastal Cottage on Private Island, overlooking the Essex Great Marsh

10.0 out of 10, Exceptional, (7)
"Great scenic location with very comfortable accommodations. "
Coastal Cottage on Private Island, overlooking the Essex Great Marsh

Cozy Cottage Old Fashioned Charm

9.2 out of 10, Wonderful, (81)
"Janet the owner was the the sweetest thing ever and consistently helpful with things like directions, recommendations, etc often before I even had to ask! The cottage has the tiny house feel and is perfectly located for all adventures to surrounding areas. We did Boston, Salem, Gloucester, Berlin, Rockport, Woodstock. Vermont, Concorde, New Hampshire, etc. and it made things super easy to accomplish a ton in 6 days. The town of Rockport itself is precious and I highly recommend Brothers Brew for...
Cozy Cottage Old Fashioned Charm

Glamorous Cabana: Fireplace, Holiday Lights, Luxurious Romantic, 5min to Eateries, Shopping, & Shows

9.4 out of 10, Exceptional, (26)
"We enjoyed a lovely little Anniversary getaway. The accommodations and lounging poolside simply cannot be beat- everything was so beautiful and peaceful! We also got to meet the sweetest Kipling as we were departing for home, another delightful surprise. We so thoroughly enjoyed our time there- our only complaint is we had to leave! :) "
The price is SAR 529
SAR 1,540 total
includes taxes & fees
24 Feb - 25 Feb
Glamorous Cabana: Fireplace, Holiday Lights, Luxurious Romantic, 5min to Eateries, Shopping, & Shows

WALK TO BEACH! Conveniently located! Booking for June & Sept 2025!

10.0 out of 10, Exceptional, (59)
"Our family (2 adults, 2 teens) had the most wonderful, relaxing long weekend getaway here at the Bass Ave Bungalow. The property is clean, adorably decorated/furnished, has a peaceful, open vibe, including a lovely bright kitchen, and huge cozy sectional for lounging, reading, and our favorite- family game time. The beds were comfy, kitchen was well stocked, and we absolutely loved the quaint side yard and cornhole set! We also took full advantage of the convenient location, walking distance of...
WALK TO BEACH! Conveniently located! Booking for June & Sept 2025!

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

9.8 out of 10, Exceptional, (16)
"We stayed at the Shore Cottage in Gloucester, the space was so beautiful and just enough space for my wife and I. Meghan is truly amazing and worked with us for an early check-in in such a timely manner, we felt so welcomed and truly appreciated our little welcome basket as well as our stay! We recommend Gloucester and The Shore Cottage to everyone! Thank you so much for such a wonderful Weekend Getaway! "
Shore Cottage - Coastal gem, a traveler favorite! Outdoor patio, central AC.

Rockport Cottage w/ Patio - Steps to Beach!

2.0 star property
Rockport Cottage w/ Patio - Steps to Beach!

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

2.0 star property
9.8 out of 10, Exceptional, (8)
"Place was in a great location. Short walk to the beach."
Plum Island Beach Cottage - 4 Minute Walk To Beach!!

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

9.2 out of 10, Wonderful, (10)
"When we arrived we were immediately struck by how spotlessly clean the whole cabin was. And there were very thoughtful welcome packs too. The cabin has quaint cottage touches and the surround sounds from the woods were lovely. Very relaxing and comfortable environment. Full-sized washer and dryer came in handy. Don’t miss America’s Stonehenge just up the road. Would happily stay here again."
Big Fish, Little Pond. Fire Pit Swimming, Hiking, Kayaking, and Fishing!

The PondeRosa cottage at Cobbett's pond

10.0 out of 10, Exceptional, (19)
"Location worked perfect for us to be near family and friends "
The PondeRosa cottage at Cobbett's pond

The Birdhouse • Woodland Retreat • Gloucester+Essex • Firepit • Outdoor shower

10.0 out of 10, Exceptional, (13)
"We spent a lovely wintertime weekend in the birdhouse. Location was great: within walking distance from Conomo Beach and 15 min drive to Gloucester’s center. The house is very comfortable with everything we needed (though we didn’t cook). Check-in and check-out were very simple and the host super responsive. We already plan to come back. "
The Birdhouse • Woodland Retreat • Gloucester+Essex • Firepit • Outdoor shower

Plum Island Guest Cottage With Water View

9.8 out of 10, Exceptional, (56)
"I really enjoyed my stay at the cottageIt was very comfortable. I'm so happy that I could bring my dogs. It was close to my son and daughter in law! Loved it! "
Plum Island Guest Cottage With Water View

Ipswich Cottage: Beautiful Views, 5 Mins to Beach

8.4 out of 10, Very Good, (19)
"The views were excellent! The house was perfect for a group! We could have used a microwave but the oven worked for heating up food. It was peaceful and quiet after roaming around Salem."
Ipswich Cottage: Beautiful Views, 5 Mins to Beach

Seaside Getaway Cottage w Deck, Parking, Ocean View, Shops

10.0 out of 10, Exceptional, (4)
"Loved every minute of it. Excellent location directly at the water and the shops and restaurants. The house is very well appointed with new and modern appliances and bathroom. Beds were super comfy and house is very cozy and super clean. The deck/balcony with view on the water is wonderful. The house is very quiet. Communication with the owner is excellent and check in and check out process are straightforward and easy. The owner really goes above and beyond to make this a memorable and...
Seaside Getaway Cottage w Deck, Parking, Ocean View, Shops

Modern Cottage, Private Island, Unparalleled beauty

9.4 out of 10, Exceptional, (3)
"Loved the property. Very secluded and quiet. Nice place to stay if you’re going to Salem "
Modern Cottage, Private Island, Unparalleled beauty

Cozy Cottage 3 min walk to Plum Island Beach

9.6 out of 10, Exceptional, (15)
"This home is as amazing as the owners who loaned it to us for a week. They keep it So clean and cozy, with everything you need for a great vacation. So much room inside and outside. The horseshoe pits and corn hole was an added plus which we took full advantage of. Walking distance to everything and we were able to walk to the beach every morning to see the sunrise . Would recommend this property to anyone unless it’s the week that we want to rent it.😊"
Cozy Cottage 3 min walk to Plum Island Beach

Cozy oceanfront home with unique architecture

7.6 out of 10, Good, (36)
"There's no other residence in sight from this lovely, quiet, waterfront setting just a mile from town. The house is vintage in all ways (except for one minisplit), a delightful step back in time. This includes the very basic and cramped kitchen, which was fine with us. We still did plenty of cooking and happily washed our own dishes--again, an old-school vacation. I suspect the house would be pretty hot in a heat wave, as all rooms except the main living/dining room are cooled with fans only,...
Cozy oceanfront home with unique architecture

Little Pond, Big Fish, Swimming, Hiking, Kayaking on our Private Lake.

9.2 out of 10, Wonderful, (5)
"The cabin is in a very nice, quiet and peaceful area. The property was clean and inviting. Once we figured how to work the pellet heater we were set. We were very pleased with our stay. "
Little Pond, Big Fish, Swimming, Hiking, Kayaking on our Private Lake.
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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Other property types in Middleton

Sonder 907 Main

4.0 star property
8.2 out of 10, Very Good, (433)
"Clean, spacious room/bathroom, convenient. "
The price is SAR 512
SAR 594 total
includes taxes & fees
2 Mar - 3 Mar
Sonder 907 Main

No. 284 powered by Sonder

4.0 star property
9.4 out of 10, Exceptional, (868)
"my favorite stay ever. i loved my stay and everything about it and can’t wait to come back soon. "
The price is SAR 577
SAR 681 total
includes taxes & fees
26 Feb - 27 Feb
No. 284 powered by Sonder

Temple Place Suites

2.5 star property
6.8 out of 10, (182)
"Insane lil spot for seeing Boston and surrounding areas!"
The price is SAR 360
SAR 620 total
includes taxes & fees
24 Feb - 25 Feb
Temple Place Suites
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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