A coastal town with a lighthouse, houses, and a river.

Holiday Rentals in Middlesex County

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Our top choices for Middlesex County holiday rentals

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Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
2.5 star property
East Haddam
9.6 out of 10, Exceptional, (160 reviews)
"Great stay! "
United States
Tanitra
The price is €211
includes taxes & fees
30 Jun - 1 Jul
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
1 bedroom, desk, iron/ironing board, travel cot

1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (46 reviews)
"We enjoyed our stay"
United States
JM B.
The price is €244
includes taxes & fees
1 Jul - 2 Jul
1-bedroom cottage with Grove Beach 🏖️ access.
Fridge, microwave, oven, stovetop

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

The gardners Cottage 1 mile from long Island Sound - pet friendly
Clinton
10.0 out of 10, Exceptional, (24 reviews)
"Enjoyed our stay - Highly recommend!"
United States
Mary S.
The price is €444
includes taxes & fees
1 Jul - 2 Jul
The gardners Cottage 1 mile from long Island Sound - pet friendly
Interior

New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.

New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
Durham
9.8 out of 10, Exceptional, (28 reviews)
"Wonderful house in a great location."
United States
Edward S.
The price is €922
includes taxes & fees
28 Jun - 29 Jun
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
Beach nearby

adorable ranch in beach community

adorable ranch in beach community
Old Saybrook
10.0 out of 10, Exceptional, (45 reviews)
"The experience was a pleasure - the house is comfy, and the location amazing! "
United States
Matthew V.
The price is €751
includes taxes & fees
15 Jul - 16 Jul
adorable ranch in beach community
Dining

Adorable Cottage with Cottage porch, walk to water & town

Adorable Cottage with Cottage porch, walk to water & town
Westbrook Center
8.8 out of 10, Excellent, (6 reviews)
"Great host and property"
United States
Kevin K.
The price is €633
includes taxes & fees
24 Jul - 25 Jul
Adorable Cottage with Cottage porch, walk to water & town
Property grounds

#24 *Serenity* A Lakefront Cottage Retreat

#24 *Serenity* A Lakefront Cottage Retreat
Middletown
9.8 out of 10, Exceptional, (23 reviews)
"It was great "
United States
Rodrigo C.
The price is €393
includes taxes & fees
29 Jun - 30 Jun
#24 *Serenity* A Lakefront Cottage Retreat
Exterior

Walk To Goodspeed Opera House!

Walk To Goodspeed Opera House!
East Haddam
9.4 out of 10, Exceptional, (38 reviews)
"Needed a one night stay - worked fine"
United States
Michelle B.
The price is €280
includes taxes & fees
28 Jun - 29 Jun
Walk To Goodspeed Opera House!
Dining

Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included

Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included
Old Saybrook
9.8 out of 10, Exceptional, (38 reviews)
"Enjoyed our stay"
United States
Nicole L.
Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included
Beach

Beachside Bliss w/ Game Room, Gym & Golf Green

Beachside Bliss w/ Game Room, Gym & Golf Green
Westbrook
10.0 out of 10, Exceptional, (1 review)
"Perfect house for 6 guests. Loved that it was close to the beach."
United States
Shannon G.
The price is €702
includes taxes & fees
1 Jul - 2 Jul
Beachside Bliss w/ Game Room, Gym & Golf Green
Exterior

Driftwood Cottage @ Saybrook Point Marina, 2 King Beds

Driftwood Cottage @ Saybrook Point Marina, 2 King Beds
Old Saybrook Center
9.6 out of 10, Exceptional, (49 reviews)
"Lovely cottage! Enjoyed our stay! "
United States
Joyce S.
The price is €693
includes taxes & fees
12 Jul - 13 Jul
Driftwood Cottage @ Saybrook Point Marina, 2 King Beds
Interior

Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats

Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats
Saybrook Manor
9.8 out of 10, Exceptional, (139 reviews)
"Yvette was so communicative and made the stay great! The house was amazing and everything was cozy and comfortable. It was great for a group!"
United States
Hayley T.
The price is €625
includes taxes & fees
1 Jul - 2 Jul
Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats
Interior

Conference Room Rental no sleeping arrangements

Conference Room Rental no sleeping arrangements
Main Street Historic District
The price is €809
includes taxes & fees
11 Jul - 12 Jul
Conference Room Rental no sleeping arrangements
Smart TV, fireplace, books, music library

Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown

Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
Haddam
10.0 out of 10, Exceptional, (33 reviews)
"Fantastic experience from beginning to end! Loved every minute of my stay! "
United States
Jody U.
The price is €267
includes taxes & fees
15 Jul - 16 Jul
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
Property grounds

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

Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!
Lake Pocotopaug
10.0 out of 10, Exceptional, (16 reviews)
"Clean, quiet, beautiful surroundings and a great host"
United States
Jennifer J.
The price is €307
includes taxes & fees
23 Jul - 24 Jul
Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!
Property grounds

NEW Coastal Cottage 2 Miles to Beach + Lake Access

NEW Coastal Cottage 2 Miles to Beach + Lake Access
Clinton
10.0 out of 10, Exceptional, (5 reviews)
The price is €278
includes taxes & fees
30 Jun - 1 Jul
NEW Coastal Cottage 2 Miles to Beach + Lake Access
Exterior

Family Stays: Middletown, CT

Family Stays: Middletown, CT
Middletown
10.0 out of 10, Exceptional, (28 reviews)
"House is immaculate and the hosts were great! Made is feel very welcome. Would definitely stay again!"
United States
Diana C.
Family Stays: Middletown, CT
Dining

3 BR Apartment Near Wesleyan 202

3 BR Apartment Near Wesleyan 202
Washington Street Historic District
8.0 out of 10, Very good, (1 review)
"The apartment is the first floor of a two story duplex. It was very clean and larger than we were expecting. We had just about everything we needed for our stay. We really appreciate being able to bring our pets with us. I enjoyed walking around the neighborhood with my dog."
United States
Douglas M.
The price is €341
includes taxes & fees
30 Jun - 1 Jul
3 BR Apartment Near Wesleyan 202
Beach nearby

1st Floor Westbrook Anchor | 2 Queen Beds | EV Charger | Near Beach

1st Floor Westbrook Anchor | 2 Queen Beds | EV Charger | Near Beach
Westbrook Center
The price is €391
includes taxes & fees
28 Jun - 29 Jun
1st Floor Westbrook Anchor | 2 Queen Beds | EV Charger | Near Beach
Fridge, microwave, oven, stovetop

Private Apt in Middletown-Wesleyan 101

Private Apt in Middletown-Wesleyan 101
Washington Street Historic District
7.4 out of 10, Good, (3 reviews)
"Very clean. No frills."
United States
Kristoph
The price is €280
includes taxes & fees
29 Jun - 30 Jun
Private Apt in Middletown-Wesleyan 101
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 Middlesex County Hotel Reviews

Best Western Mystic Hotel

Best Western Mystic Hotel

8/10 Good
"Staff were helpful and pleasant. Bathrooms are dated but clean. Humid feeling in the room even with AC going. Will return in less muggy weather"
Liza 1-night trip
Posted 2 hours ago
Best Western Mystic Hotel

Find out more about Middlesex County

Holiday Homes in Middlesex County

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