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Compare 59 Cottages in Middleton with updated reviews, rates, and availability.

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

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

9.6 out of 10, Exceptional, (30)
"Exactly how it was described clean easy to get to! Highly recommended "
Luxury 1900's romantic retreat steps from the beach - King Suite!
Good Harbor Beach House - walk to beach, close to restaurants and shopping!
Entrance to Good Harbor Beach just down the street!

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

10.0 out of 10, Exceptional, (194)
"Great time in Gloucester for the ancient mariner hockey tourney. The owners are so easy to work with and the home is beautiful!"
Good Harbor Beach House - walk to beach, close to restaurants and shopping!
Cozy Cottage Old Fashioned Charm
Terrace/patio

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
Coastal Cottage on Private Island, overlooking the Essex Great Marsh
Miscellaneous

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
Cottage with Direct Water Access!
Living area

Cottage with Direct Water Access!

10.0 out of 10, Exceptional, (107)
"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!
The Shore House, steps to the ocean meet crisp clean beach side retreat!
Beach

The Shore House, steps to the ocean meet crisp clean beach side retreat!

8.0 out of 10, Very Good, (2)
"The house was quite lovely. We were expecting 2 rooms with twin beds but there was just 1 room with twin beds. Downstairs space was great. We were surprised that there wasn’t an outdoor space to barbecue and have dinner for a group. Deck was small so great for coffee but not a meal at the end of the day. There were some beach towels and bath towels but we expected more towels. AC worked well. The 1 bathroom was small. It would have helped to at least have an outdoor shower. For the price of our...
The Shore House, steps to the ocean meet crisp clean beach side retreat!
Glamorous Cabana: Fireplace, Holiday Lights, Luxurious Romantic, 5min to Eateries, Shopping, & Shows
Twinkling holiday lights

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 417
SAR 1,396 total
includes taxes & fees
23 Dec - 24 Dec
Glamorous Cabana: Fireplace, Holiday Lights, Luxurious Romantic, 5min to Eateries, Shopping, & Shows
Shore Cottage - Coastal gem, a traveler favorite! Outdoor patio, central AC.
Exterior detail

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.
WALK TO BEACH! Conveniently located! Booking for June & Sept 2025!
Brand new kitchen with oversized slider to take you onto the back patio

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

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

10.0 out of 10, Exceptional, (18)
"We had a wonderful and comfortable stay. The owner was gracious and got back to us immediately with answers to our questions. Being so close to the beach and able to hear the ocean was so soothing. Would highly recommend this to anyone."
Adorable Beach house with lots of outdoor space and steps to Long Beach!
PERIWINKLE COTTAGE #2 - OPEN ALL YEAR - walk to everything, parking, wifi, quiet
1

PERIWINKLE COTTAGE #2 - OPEN ALL YEAR - walk to everything, parking, wifi, quiet

10.0 out of 10, Exceptional, (160)
"Cozy and comfortable property in Rockport. Great communications from host. Easy walk to town and train. Ideal base to explore the historic towns and natural beauty of Cape Ann. The weather was wonderful, and colors of the leaves were peaking. One of our best getaways! Highly recommended! "
PERIWINKLE COTTAGE #2 - OPEN ALL YEAR - walk to everything, parking, wifi, quiet
The PondeRosa cottage at Cobbett's pond
Our cozy master bedroom with a queen size bed

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
Perch from the upstairs balcony on this cozy swing

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

10.0 out of 10, Exceptional, (12)
"The property is so beautiful and super serene.. there weren't chairs by the fire pit sadly and the tv lags maybe cause of Internet idk so we were trying to watch the Yankees game and couldn't and had to on our phones. Id still love to visit in the summer and go to the ocean and stuff."
The Birdhouse • Woodland Retreat • Gloucester+Essex • Firepit • Outdoor shower
Cozy Cottage 3 min walk to Plum Island Beach
Exterior

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
Plum Island Guest Cottage With Water View
Plum Island Guest House

Plum Island Guest Cottage With Water View

9.8 out of 10, Exceptional, (54)
"Best ever!"
Plum Island Guest Cottage With Water View
Ipswich Cottage: Beautiful Views, 5 Mins to Beach
Ipswich Vacation Rental | 4BR | 2BA | 1,200 Sq Ft | 1 Step for Entry

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
Big Fish, Little Pond. Fire Pit Swimming, Hiking, Kayaking, and Fishing!
The Firepit! Make a cocktail and warm up!

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

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
Plum Island Beautiful views weekly summer rental
Exterior

Plum Island Beautiful views weekly summer rental

8.8 out of 10, Excellent, (14)
"Beautiful Breezy little cottage right on the Tidal Basin and a 13 minute walk to the ocean side beach. Wonderful quiet little neighborhood with friendly neighbors and everything you need at the rental, including two lovely porches to relax on. Great place."
Plum Island Beautiful views weekly summer rental
Spacious Beach House with Spectacular Ocean Views and Private Beach Access
Relax on your porch and enjoy 180 degree views of the beach, ocean and sunsets

Spacious Beach House with Spectacular Ocean Views and Private Beach Access

10.0 out of 10, Exceptional, (29)
"Great place. Roomy, tasteful decor, all the amenities one could want, awesome ocean view from the covered porch, and lots of things to doneaeby. Host is very pleasant, helpful, and thinks of everything. Can’t wait to return"
Spacious Beach House with Spectacular Ocean Views and Private Beach Access
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
Room

Sonder 907 Main

4.0 star property
8.2 out of 10, Very Good, (405)
"Perfect location!"
The price is SAR 483
SAR 560 total
includes taxes & fees
23 Dec - 24 Dec
Sonder 907 Main
Maverick Suites at 28 Fenway
Lobby sitting area

Maverick Suites at 28 Fenway

3.0 star property
9.0 out of 10, Wonderful, (156)
"Great stay. "
The price is SAR 372
SAR 795 total
includes taxes & fees
24 Dec - 25 Dec
Maverick Suites at 28 Fenway
Temple Place Suites
Room

Temple Place Suites

2.5 star property
6.8 out of 10, (175)
"I recently had the pleasure of staying at Temple Place Suites, and I can honestly say it you get what you pay for. The location is absolutely perfect, situated in the heart of the city, with easy access to vibrant neighborhoods, restaurants, and cultural landmarks. The suite is minimalistic and there’s a sense of homeliness. Spacious, impeccably clean, and tastefully decorated. The staff at Temple Place Suites went above and beyond to make my stay memorable. They were friendly, attentive, and...
The price is SAR 361
SAR 621 total
includes taxes & fees
23 Dec - 24 Dec
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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