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

Vacation Rentals in Middlesex County

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Our top choices for Middlesex County vacation 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, (163 reviews)
"Great stay! "
United States
Tanitra
The price is ￥27,386
￥38,948 total
includes taxes & fees
Jul 12 - Jul 13
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
1 bedroom, desk, iron/ironing board, travel crib

1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (47 reviews)
"We enjoyed our stay"
United States
JM B.
The price is ￥23,189
￥41,715 total
includes taxes & fees
Jul 13 - Jul 14
1-bedroom cottage with Grove Beach 🏖️ access.
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)
"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 ￥24,489
￥47,178 total
includes taxes & fees
Jul 15 - Jul 16
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
Exterior

Walk To Goodspeed Opera House!

Walk To Goodspeed Opera House!
East Haddam
9.4 out of 10, Exceptional, (39 reviews)
"Needed a one night stay - worked fine"
United States
Michelle B.
The price is ￥27,224
￥45,001 total
includes taxes & fees
Jul 15 - Jul 16
Walk To Goodspeed Opera House!
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 ￥39,739
￥74,243 total
includes taxes & fees
Jul 22 - Jul 23
#24 *Serenity* A Lakefront Cottage Retreat
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, (17 reviews)
"Clean, quiet, beautiful surroundings and a great host"
United States
Jennifer J.
The price is ￥27,873
￥55,713 total
includes taxes & fees
Aug 3 - Aug 4
Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!
Dining

3 BR Apartment Near Wesleyan 201

3 BR Apartment Near Wesleyan 201
Washington Street Historic District
The price is ￥22,056
￥53,422 total
includes taxes & fees
Jul 9 - Jul 10
3 BR Apartment Near Wesleyan 201
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 ￥53,579
￥101,641 total
includes taxes & fees
Jul 16 - Jul 17
#29 - Modern 5 Bedroom/2 Bath
Beach nearby

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 ￥32,397
￥68,652 total
includes taxes & fees
Jul 22 - Jul 23
Private 2nd-Floor Apt | 4 Mins to Beach | EV Charger & Parking Included
Fridge, microwave, oven, stovetop

Private Apt in Middletown-Wesleyan 101

Private Apt in Middletown-Wesleyan 101
Washington Street Historic District
7.0 out of 10, Good, (4 reviews)
"Very clean. No frills."
United States
Kristoph
The price is ￥26,273
￥57,947 total
includes taxes & fees
Jul 29 - Jul 30
Private Apt in Middletown-Wesleyan 101
Fridge, microwave, oven, stovetop

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 ￥40,513
￥51,613 total
includes taxes & fees
Jul 16 - Jul 17
3-bedroom Unit in tranquil Middletown
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, (6 reviews)
The price is ￥79,405
￥102,335 total
includes taxes & fees
Jul 9 - Jul 10
NEW Coastal Cottage 2 Miles to Beach + Lake Access
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 ￥70,492
￥132,112 total
includes taxes & fees
Jul 28 - Jul 29
Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats
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 ￥52,366
￥98,545 total
includes taxes & fees
Aug 1 - Aug 2
Adorable Cottage with Cottage porch, walk to water & town
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 ￥81,025
￥136,203 total
includes taxes & fees
Jul 15 - Jul 16
adorable ranch in beach community
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 ￥82,062
￥137,558 total
includes taxes & fees
Jul 12 - Jul 13
Driftwood Cottage @ Saybrook Point Marina, 2 King Beds
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 ￥105,333
￥163,833 total
includes taxes & fees
Jul 15 - Jul 16
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
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 ￥95,901
￥177,415 total
includes taxes & fees
Aug 2 - Aug 3
Beachside Bliss w/ Game Room, Gym & Golf Green
Interior

Conference Room Rental no sleeping arrangements

Conference Room Rental no sleeping arrangements
Main Street Historic District
The price is ￥116,676
￥150,869 total
includes taxes & fees
Jul 11 - Jul 12
Conference Room Rental no sleeping arrangements
Terrace/patio

PRIVATE BEACH: ROYAL OCEANVIEW CASTLE @ CLINTON W/ 4 QUEENS 2 FULL

PRIVATE BEACH: ROYAL OCEANVIEW CASTLE @ CLINTON W/ 4 QUEENS 2 FULL
Clinton
10.0 out of 10, Exceptional, (30 reviews)
"It was a very clean well kept property. The accommodation was very comfortable. We all truly enjoyed the house and location. "
United States
claire
The price is ￥190,409
￥305,505 total
includes taxes & fees
Jul 31 - Aug 1
PRIVATE BEACH: ROYAL OCEANVIEW CASTLE @ CLINTON W/ 4 QUEENS 2 FULL
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

The Capitol Hotel

The Capitol Hotel

8/10 Good
"good location and great breakfast, its in the hartford downtown area and within walking distance to the restaurants and most attractions."
Ziauddin 1-night trip
Posted 3 hours ago
The Capitol Hotel

Find out more about Middlesex County

Vacation Apartments in Middlesex County

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