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Compare 22 Cottages in Middletown with updated reviews, rates, and availability.

Private Carriage House Retreat on a 33 Acre Historic Working Estate
Exterior

Private Carriage House Retreat on a 33 Acre Historic Working Estate

10.0 out of 10, Exceptional, (11)
"Place was great !"
Private Carriage House Retreat on a 33 Acre Historic Working Estate
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Beach

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

9.8 out of 10, Exceptional, (44)
"it being off season,very quiet. the people in the surrounding neighborhood were very friendly, we had a great time, ash and christine were awsome host. we will deffinately go back again!"
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
A cottage on the shore of the Delaware River
Exterior detail

A cottage on the shore of the Delaware River

9.8 out of 10, Exceptional, (59)
"The coziest house we have ever stayed at ! The host went above and beyond to have everything we could need! Would definitely recommend ! "
A cottage on the shore of the Delaware River
Quarry Landing - Center of Town & River View - 3 Bedroom
Room

Quarry Landing - Center of Town & River View - 3 Bedroom

9.8 out of 10, Exceptional, (7)
"On a small hillside. Very quaint accommodation. Close to restaurants and river. Parking a little difficult to figure out, train is a bit loud and frequent but everything else was as advertised and nice. "
The price is SAR 556
SAR 864 total
includes taxes & fees
5 Jan - 6 January 2025
Quarry Landing - Center of Town & River View - 3 Bedroom
Family-Friendly Cottage, Walk to the Beach!
Kennedyville Vacation Rental | 2BR | 1BA | 4 Stairs to Access | 1,000 Sq Ft

Family-Friendly Cottage, Walk to the Beach!

10.0 out of 10, Exceptional, (18)
"Another amazing stay at Robin’s Rest. Highly recommend for a quiet weekend getaway "
Family-Friendly Cottage, Walk to the Beach!
Thunder Hill Retreat - Peaceful - sleeps 12

Thunder Hill Retreat - Peaceful - sleeps 12

10.0 out of 10, Exceptional, (9)
"In the area to move our daughter in to her sophomore year of college"
The price is SAR 998
SAR 2,109 total
includes taxes & fees
6 Jan - 7 January 2025
Thunder Hill Retreat - Peaceful - sleeps 12
Chesapeake Romantic Waterfront Home with Private Pool
Pool closed in winter and virtually staged because it was closed during pic.

Chesapeake Romantic Waterfront Home with Private Pool

8.8 out of 10, Excellent, (5)
"Great communication, easy to access, accommodations true to listing. Spacious, renovated living space. Great outdoor pool."
Chesapeake Romantic Waterfront Home with Private Pool
Elsinboro Retreat I 3BR I 2BA I - enjoy fishing , hunting, jet skiing,& hiking.
Exterior

Elsinboro Retreat I 3BR I 2BA I - enjoy fishing , hunting, jet skiing,& hiking.

8.8 out of 10, Excellent, (3)
"Enjoyed our stay. House was perfect for the 2 of us. Definitely better than staying in a noisy hotel!"
Elsinboro Retreat I 3BR I 2BA I - enjoy fishing , hunting, jet skiing,& hiking.
Be persuaded to experience this vintage cottage by the Sassa
Outdoor dining

Be persuaded to experience this vintage cottage by the Sassa

9.4 out of 10, Exceptional, (8)
"We had one of the best vacations ever. Our 9 and 7 year old grandchildren wanted to live there forever! We had a beautiful house and access to the outdoor spaces including a dock for gishing, crabbing and swimming. We were able to make smores over a great fire pit and enjoyed phenominal sunsets from a sitting area overlooking the river. Gene and Suzie, the hosts were on-site and so warm and welcoming. Our every need was met immediately. We will definitely be vacationing at Gregg Neck Cottage...
Be persuaded to experience this vintage cottage by the Sassa
Waterfront Cottage on the C&D Canal!
Exterior

Waterfront Cottage on the C&D Canal!

8.0 out of 10, Very Good, (5)
"Fantastic location "
Waterfront Cottage on the C&D Canal!
Waterfront cottage in historic Charlestown, Maryland
Aerial view

Waterfront cottage in historic Charlestown, Maryland

9.6 out of 10, Exceptional, (5)
"It was hot the week we stayed, and the ac could not keep up. and the creek was too low to kayak to the bay. It was a short walk to the beach which was nice. All and all it was a nice stay. "
Waterfront cottage in historic Charlestown, Maryland
Vintage Waterfront Cottage with Stunning Sunsets
Beach

Vintage Waterfront Cottage with Stunning Sunsets

10.0 out of 10, Exceptional, (5)
"thoroughly enjoyed our time at this lovely property. the quiet location, attention to detail, and communication with owners all made for an delightful stay. "
Vintage Waterfront Cottage with Stunning Sunsets
Waterfront Historical District Home Near River
Living area

Waterfront Historical District Home Near River

3.0 star property
Waterfront Historical District Home Near River
Long Beach Cottage, (romantic couple’s getaway)

Long Beach Cottage, (romantic couple’s getaway)

10.0 out of 10, Exceptional, (3)
"We had a wonderful time! Being near the water is my happy place. The size of the home is perfect for me. And the weather was perfect! Thank you!"
The price is SAR 1,111
SAR 1,779 total
includes taxes & fees
5 Jan - 6 January 2025
Long Beach Cottage, (romantic couple’s getaway)
Sunset River Shack - Waterfront Boho Cottage on the Elk River /Chesapeake Bay
Terrace/patio

Sunset River Shack - Waterfront Boho Cottage on the Elk River /Chesapeake Bay

2.0 star property
9.0 out of 10, Wonderful, (2)
"The home is nice The view from the deck was wonderful But there wasn’t access to the water Easy to find and we really enjoyed the area"
Sunset River Shack - Waterfront Boho Cottage on the Elk River /Chesapeake Bay
Charming 2-bedroom water oriented cottage with water access
Exterior

Charming 2-bedroom water oriented cottage with water access

Charming 2-bedroom water oriented cottage with water access
Adorable 100-year-old tiny home in historic town. Gym membership included!
Exterior

Adorable 100-year-old tiny home in historic town. Gym membership included!

10.0 out of 10, Exceptional, (1)
Adorable 100-year-old tiny home in historic town. Gym membership included!
Family-friendly Cottage, Walk to the Beach!
Living area

Family-friendly Cottage, Walk to the Beach!

3.0 star property
Family-friendly Cottage, Walk to the Beach!
Wilmington Home ~ 28 Mi to Downtown Philadelphia!
Property grounds

Wilmington Home ~ 28 Mi to Downtown Philadelphia!

3.0 star property
Wilmington Home ~ 28 Mi to Downtown Philadelphia!
Waterfront Millington Vacation Rental w/ Hot Tub!
Property grounds

Waterfront Millington Vacation Rental w/ Hot Tub!

3.0 star property
Waterfront Millington Vacation Rental w/ Hot Tub!
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 Middletown

Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay
Bluffside seating overlooking the Chesapeake Bay

Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay

10.0 out of 10, Exceptional, (75)
"We had a great two days here! House has everything you need. We really enjoyed the hot tub! We were lucky the weather was so warm and we could just sit outside all day looking at the water and end the day with gorgeous sunsets. We would definitely come back!"
Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Beach

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

9.8 out of 10, Exceptional, (44)
"it being off season,very quiet. the people in the surrounding neighborhood were very friendly, we had a great time, ash and christine were awsome host. we will deffinately go back again!"
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Super cute 3 bedroom remodeled townhouse near downtown Wilmington
Room

Super cute 3 bedroom remodeled townhouse near downtown Wilmington

8.8 out of 10, Excellent, (11)
"Amazing stay. nice quiet clean home. Accommodating for the whole family. Host was easy to connect with very helpful loved our stay ! Looking forward to booking again."
Super cute 3 bedroom remodeled townhouse near downtown Wilmington
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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