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
2.0 star property
East Haddam
9.6 out of 10, Exceptional, (130 reviews)
"Clean rooms - great place "
United States
Sebastian
The price is €139
includes taxes & fees
31 Mar - 1 Apr
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
Exterior

Walk To Goodspeed Opera House!

Walk To Goodspeed Opera House!
East Haddam
9.4 out of 10, Exceptional, (35 reviews)
"Place was clean, beds were comfortable. We were only there one night but was well worth it."
United States
Annette L.
The price is €163
includes taxes & fees
31 Mar - 1 Apr
Walk To Goodspeed Opera House!
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, (26 reviews)
"Wonderful house in a great location."
United States
Edward S.
The price is €848
includes taxes & fees
1 Apr - 2 Apr
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
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, (28 reviews)
"Fantastic experience from beginning to end! Loved every minute of my stay! "
United States
Jody U.
The price is €224
includes taxes & fees
4 Apr - 5 Apr
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
Exterior detail

Shoreline Oasis

Shoreline Oasis
Clinton
9.2 out of 10, Wonderful, (7 reviews)
"Everything was as advertised or better. Lovely quiet area near beautiful beaches and great restaurants. We had a terrific experience. "
United States
Tom S.
The price is €228
includes taxes & fees
24 Apr - 25 Apr
Shoreline Oasis
Interior

Conference Room Rental no sleeping arrangements

Conference Room Rental no sleeping arrangements
Main Street Historic District
The price is €802
includes taxes & fees
10 Apr - 11 Apr
Conference Room Rental no sleeping arrangements
Interior

Cozy Guest Suite in Historic Home

Cozy Guest Suite in Historic Home
Middletown
10.0 out of 10, Exceptional, (1 review)
"Perfect for a single traveler. Clean, roomy, quaint room. "
United States
Brooke
The price is €188
includes taxes & fees
30 Mar - 31 Mar
Cozy Guest Suite in Historic Home
Exterior

Family Stays: Middletown, CT

Family Stays: Middletown, CT
Middletown
10.0 out of 10, Exceptional, (23 reviews)
"A truly wonderful experience! The host and home were amazing and we’ll definitely be staying here again!"
United States
Harmony R.
Family Stays: Middletown, CT
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, (43 reviews)
"Lovely cottage! Enjoyed our stay! "
United States
Joyce S.
The price is €442
includes taxes & fees
29 Mar - 30 Mar
Driftwood Cottage @ Saybrook Point Marina, 2 King Beds
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 €463
includes taxes & fees
31 Mar - 1 Apr
Beachside Bliss w/ Game Room, Gym & Golf Green
Interior

Modern 3BR New Build AVAILABLE FOR TRAVELERS CHAMPIONSHIP GOLF TOURNAMENT!!

Modern 3BR New Build AVAILABLE FOR TRAVELERS CHAMPIONSHIP GOLF TOURNAMENT!!
Cromwell
The price is €1,004
includes taxes & fees
1 Apr - 2 Apr
Modern 3BR New Build AVAILABLE FOR TRAVELERS CHAMPIONSHIP GOLF TOURNAMENT!!
Smart TV

3-bedroom Unit in tranquil Middletown

3-bedroom Unit in tranquil Middletown
Washington Street Historic District
7.2 out of 10, Good, (5 reviews)
"Nice place"
United States
Jousette C.
The price is €244
includes taxes & fees
30 Mar - 31 Mar
3-bedroom Unit in tranquil Middletown
Interior

East Haddam Lake View Rental

East Haddam Lake View Rental
East Haddam
The price is €395
includes taxes & fees
5 Apr - 6 Apr
East Haddam Lake View Rental
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, (39 reviews)
"Many local restaurants near by. Christy's for breakfast was very good. "
United States
Benjamin H.
The price is €178
includes taxes & fees
30 Mar - 31 Mar
1-bedroom cottage with Grove Beach 🏖️ access.
Smart TV

#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 €366
includes taxes & fees
29 Mar - 30 Mar
#29 - Modern 5 Bedroom/2 Bath
Property grounds

Stylish Modern Stay Steps from the Ocean

Stylish Modern Stay Steps from the Ocean
Clinton
10.0 out of 10, Exceptional, (1 review)
"Very Clean and New. Location very convenient to Shopping , Coffee and Winery. Place very very small but Shower was huge and token gifts such as wine and toiletries a big plus . As well as guest for TV for Netflix. Added bonus outdoor space makes up for lack of living room. I would recommend this place and stay again for sure. Also, conveniently located to major highway and safe. "
United States
Kelly Z.
The price is €247
includes taxes & fees
5 Apr - 6 Apr
Stylish Modern Stay Steps from the Ocean
Fridge, microwave, oven, stovetop

Private Apt in Middletown-Wesleyan 101

Private Apt in Middletown-Wesleyan 101
Washington Street Historic District
6.0 out of 10, (2 reviews)
"The apartment was exactly what we needed to rest between events at Wesleyan. Good communication, fixed an air conditioner and added one prior to our arrival (and it was very very hot. So it was appreciated."
United States
Carolyn O.
The price is €238
includes taxes & fees
29 Mar - 30 Mar
Private Apt in Middletown-Wesleyan 101
Dining

3 BR Apartment Near Wesleyan 202

3 BR Apartment Near Wesleyan 202
Washington Street Historic District
The price is €286
includes taxes & fees
29 Mar - 30 Mar
3 BR Apartment Near Wesleyan 202
Fridge, microwave, oven, stovetop

2BR Apartment Near Wesleyan 301

2BR Apartment Near Wesleyan 301
Washington Street Historic District
10.0 out of 10, Exceptional, (1 review)
"The living quarters was clean, no bugs, essentials provided (except laundry detergent and hair dryer), quiet residence, muddy parking lot, safe neighborhood, great communication and ease of parking and entry. "
United States
Joanne L.
The price is €240
includes taxes & fees
29 Mar - 30 Mar
2BR Apartment Near Wesleyan 301
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 €357
includes taxes & fees
27 Apr - 28 Apr
1st Floor Westbrook Anchor | 2 Queen Beds | EV Charger | Near Beach
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

Hampton Inn & Suites Hartford/East Hartford

Hampton Inn & Suites Hartford/East Hartford

6/10 Okay
"The breakfast was good and the room was clean and there was lots of parking. The was water in the room was very cold. We were locked out of our room due to the battery issues on our key."
Barbara 1-night trip
Posted 2 hours ago
Hampton Inn & Suites Hartford/East Hartford

Find out more about Middlesex County

Holiday Homes in Middlesex County

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