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

Middlesex County Holiday Rentals

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Our top choices for Middlesex County holiday rentals

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, (163 reviews)
"Great experience at usual."
United States
Andrea
The price is HK$1,058
HK$1,578 total
includes taxes & fees
11 Aug - 12 Aug
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (47 reviews)
The price is HK$1,122
HK$2,026 total
includes taxes & fees
13 Jul - 14 Jul
1-bedroom cottage with Grove Beach 🏖️ access.

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)
"My son and I were here for two nights and had an excellent time. It was exactly as described and such a tastefully decorated and maintained place to stay. Would definitely stay here again if in the area!"
United States
Kate F.
The price is HK$1,129
HK$2,178 total
includes taxes & fees
20 Jul - 21 Jul
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown

#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 HK$1,669
HK$3,229 total
includes taxes & fees
5 Aug - 6 Aug
#24 *Serenity* A Lakefront Cottage Retreat

2BR Apartment Near Wesleyan 102

2BR Apartment Near Wesleyan 102
Washington Street Historic District
9.0 out of 10, Wonderful, (2 reviews)
"Excellent beds and clean."
United States
DANIEL M.
2BR Apartment Near Wesleyan 102

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, (17 reviews)
"Clean, quiet, beautiful surroundings and a great host"
United States
Jennifer J.
The price is HK$1,215
HK$2,526 total
includes taxes & fees
3 Aug - 4 Aug
Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!

Walk To Goodspeed Opera House!

Walk To Goodspeed Opera House!
East Haddam
9.4 out of 10, Exceptional, (40 reviews)
"Needed a one night stay - worked fine"
United States
Michelle B.
The price is HK$1,387
HK$2,274 total
includes taxes & fees
16 Jul - 17 Jul
Walk To Goodspeed Opera House!

The Beach Nest-Lux Cottage Steps to the Beach

The Beach Nest-Lux Cottage Steps to the Beach
Clinton
9.8 out of 10, Exceptional, (6 reviews)
"This is exactly what we needed. Nice area, great place to walk, easy to relax. "
United States
Karol W.
The price is HK$2,048
HK$4,766 total
includes taxes & fees
19 Jul - 20 Jul
The Beach Nest-Lux Cottage Steps to the Beach

Private 2nd-Floor Apt | 4 Mins to Beach | EV Charger & Parking Included

Private 2nd-Floor Apt | 4 Mins to Beach | EV Charger & Parking Included
Westbrook Center
The price is HK$899
HK$2,468 total
includes taxes & fees
13 Jul - 14 Jul
Private 2nd-Floor Apt | 4 Mins to Beach | EV Charger & Parking Included

3 BR Apartment Near Wesleyan 201

3 BR Apartment Near Wesleyan 201
Washington Street Historic District
The price is HK$1,309
HK$2,901 total
includes taxes & fees
13 Jul - 14 Jul
3 BR Apartment Near Wesleyan 201

Family Stays: Middletown, CT

Family Stays: Middletown, CT
Middletown
10.0 out of 10, Exceptional, (29 reviews)
"House is immaculate and the hosts were great! Made is feel very welcome. Would definitely stay again!"
United States
Diana C.
The price is HK$1,333
HK$2,309 total
includes taxes & fees
10 Aug - 11 Aug
Family Stays: Middletown, CT

#29 - Modern 5 Bedroom/2 Bath

#29 - Modern 5 Bedroom/2 Bath
Middletown
9.4 out of 10, Exceptional, (6 reviews)
"Great place! "
United States
Gail R.
The price is HK$1,669
HK$3,683 total
includes taxes & fees
20 Jul - 21 Jul
#29 - Modern 5 Bedroom/2 Bath

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 HK$2,783
HK$5,497 total
includes taxes & fees
13 Jul - 14 Jul
Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats

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 HK$3,002
HK$5,400 total
includes taxes & fees
24 Jul - 25 Jul
Adorable Cottage with Cottage porch, walk to water & town

3-bedroom Unit in tranquil Middletown

3-bedroom Unit in tranquil Middletown
Washington Street Historic District
7.8 out of 10, Good, (6 reviews)
"Nice place"
United States
Jousette C.
The price is HK$1,960
HK$2,528 total
includes taxes & fees
14 Jul - 15 Jul
3-bedroom Unit in tranquil Middletown

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.
Driftwood Cottage @ Saybrook Point Marina, 2 King Beds

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 HK$3,919
HK$6,589 total
includes taxes & fees
15 Jul - 16 Jul
adorable ranch in beach community

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 HK$5,095
HK$8,105 total
includes taxes & fees
13 Jul - 14 Jul
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.

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 HK$3,992
HK$7,744 total
includes taxes & fees
2 Aug - 3 Aug
Beachside Bliss w/ Game Room, Gym & Golf Green

Conference Room Rental no sleeping arrangements

Conference Room Rental no sleeping arrangements
Main Street Historic District
The price is HK$5,644
HK$7,298 total
includes taxes & fees
13 Jul - 14 Jul
Conference Room Rental no sleeping arrangements
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