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Check prices for these dates

Next weekend
May 9 - May 11
In two weeks
May 16 - May 18
In one month
May 30 - Jun 1
In two months
Jun 27 - Jun 29

Browse Select Middletown Cottages

Charming 3-bedroom cottage in Old Saybrook with WiFi and AC
Living area

Charming 3-bedroom cottage in Old Saybrook with WiFi and AC

Charming 3-bedroom cottage in Old Saybrook with WiFi and AC
Charming 3-bedroom cottage short walk to Chalker Beach
Smart TV, books

Charming 3-bedroom cottage short walk to Chalker Beach

Charming 3-bedroom cottage short walk to Chalker Beach
1-bedroom cottage with Grove Beach 🏖️ access.
Smart TV

1-bedroom cottage with Grove Beach 🏖️ access.

9.2 out of 10, Wonderful, (25)
"Loved the overall stay and experience. The private beach access is a bonus"
1-bedroom cottage with Grove Beach 🏖️ access.
The gardners Cottage 1 mile from long Island Sound - pet friendly
Property grounds

The gardners Cottage 1 mile from long Island Sound - pet friendly

10.0 out of 10, Exceptional, (13)
"The cottage is cozy and clean. It has everything I need. and perfect for me and my dogs. We enjoyed our stay and had a nice winter break. We hope to come back next year. Thank you, Robin!"
The gardners Cottage 1 mile from long Island Sound - pet friendly
Enchanted Waterfront Cottage
Smart TV, fireplace, books

Enchanted Waterfront Cottage

9.0 out of 10, Wonderful, (19)
"The location was perfect. Very comfortable."
Enchanted Waterfront Cottage
Adorable New England Cottage, 2 min walk to Beach 🏖️, Available year round
Beach nearby, sun loungers, beach towels

Adorable New England Cottage, 2 min walk to Beach 🏖️, Available year round

9.8 out of 10, Exceptional, (107)
"Cute place, very clean"
Adorable New England Cottage, 2 min walk to Beach 🏖️, Available year round
Charming Westbrook Cottage, Steps to Private Beach
Microwave, coffee/tea maker, toaster, cookware/dishes/utensils

Charming Westbrook Cottage, Steps to Private Beach

10.0 out of 10, Exceptional, (3)
"Cozy cottage, good location, nice access to the Sound."
Charming Westbrook Cottage, Steps to Private Beach
Cozy cottage near downtown Clinton, Marina & Hammonasset Park
Exterior

Cozy cottage near downtown Clinton, Marina & Hammonasset Park

10.0 out of 10, Exceptional, (70)
"Perfect and cozy home base for visiting with family!"
Cozy cottage near downtown Clinton, Marina & Hammonasset Park
Beachside Twinhome: 2 Private Sides + Sunroom Escape for Friends & Family
Beach nearby, sun loungers

Beachside Twinhome: 2 Private Sides + Sunroom Escape for Friends & Family

10.0 out of 10, Exceptional, (14)
" Very clean, plenty of room for multi generational family and the beach was very relaxing. Will stay again."
Beachside Twinhome: 2 Private Sides + Sunroom Escape for Friends & Family
Beachside Branford- walk to Beach, Grill
Dining

Beachside Branford- walk to Beach, Grill

10.0 out of 10, Exceptional, (3)
"Charming little cottage that was just right for our trip to the CT shoreline."
Beachside Branford- walk to Beach, Grill
Direct waterfront renovated cottage.
TV, books

Direct waterfront renovated cottage.

10.0 out of 10, Exceptional, (71)
"Perfect stay in Madison. Beautiful location. Clean and comfy house. Will be back!"
Direct waterfront renovated cottage.
'Grandma's Cottage' w/ Sunroom: Walk to Beach
Beach nearby

'Grandma's Cottage' w/ Sunroom: Walk to Beach

8.0 out of 10, Very good, (3)
"Terrific location. 1 block from the beach."
'Grandma's Cottage' w/ Sunroom: Walk to Beach
Guilford Carriage House at Granite Lodge!
TV

Guilford Carriage House at Granite Lodge!

10.0 out of 10, Exceptional, (9)
"This was the perfect home for a relaxing girls weekend. The home was clean, comfortable and beautiful! Rebecca was a very responsive and accommodating host and I would definitely stay here again!"
Guilford Carriage House at Granite Lodge!
Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!
Miscellaneous

Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!

10.0 out of 10, Exceptional, (13)
"The place was great and we enjoyed the fishing."
Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!
Relax with a beautiful lake view
Outdoor dining

Relax with a beautiful lake view

10.0 out of 10, Exceptional, (19)
"Great location"
Relax with a beautiful lake view
Summer Cottage with Water Views at Great Hammock Beach in Old Saybrook
Beach nearby, sun loungers

Summer Cottage with Water Views at Great Hammock Beach in Old Saybrook

10.0 out of 10, Exceptional, (60)
"Wonderful stay! The hosts are friendly and communicative; the location is superb - so beautiful and you can smell the salt in the air; and the cottage was cozy and all that we needed. Thank you for a great stay!"
Summer Cottage with Water Views at Great Hammock Beach in Old Saybrook
Charming 3-bedroom cottage in Old Saybrook with AC, WiFi
Fridge, microwave, oven, dishwasher

Charming 3-bedroom cottage in Old Saybrook with AC, WiFi

Charming 3-bedroom cottage in Old Saybrook with AC, WiFi
Newly Remodeled 2 Bedroom Cottage On The Beach. The Kaitlyn Cottage
TV, stereo

Newly Remodeled 2 Bedroom Cottage On The Beach. The Kaitlyn Cottage

9.8 out of 10, Exceptional, (26)
"Beautiful place, clean , enjoyable beachside"
Newly Remodeled 2 Bedroom Cottage On The Beach. The Kaitlyn Cottage
Breathtaking Private, Lakefront Retreat.
Smart TV

Breathtaking Private, Lakefront Retreat.

Breathtaking Private, Lakefront Retreat.
A Perfect Getaway. Direct assess to the 1000 acre Old Saybrook Essex Preserve
Fridge, microwave, oven, stovetop

A Perfect Getaway. Direct assess to the 1000 acre Old Saybrook Essex Preserve

10.0 out of 10, Exceptional, (2)
"This was an amazing place to stay. Beautiful property and EXCELLENT hosts! Thank you!"
A Perfect Getaway. Direct assess to the 1000 acre Old Saybrook Essex Preserve
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

Postcard Cabins Machimoodus
Exterior

Postcard Cabins Machimoodus

2.0 star property
10.0 out of 10, Exceptional, (8)
"Loved how tranquil this site is. Was great to disconnect in nature. "
The price is CA $143
CA $220 total
includes taxes & fees
May 6 - May 7
Postcard Cabins Machimoodus
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub
Outdoor pool, a heated pool

Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub

10.0 out of 10, Exceptional, (128)
"having previously rented VRBO properties in Palm Springs, West Palm Beach & Ft. Lauderdale I can confirm this property is exceptional. The studio has 1st tier amenities, waterfront location & in addition the hosts provided most welcoming foods and snacks, an overall wonderful experienceJimBrooklyn, NY"
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub
Blue Back Bungalow
Exterior

Blue Back Bungalow

2.0 star property
9.6 out of 10, Exceptional, (10)
"Seamless check in, beautiful quaint home with excellent water pressure and hot water!Location is excellent, thank you to our hosts "
The price is CA $172
CA $529 total
includes taxes & fees
May 8 - May 9
Blue Back Bungalow
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.