Middlesex County Holiday Rentals

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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, (120 reviews)
"Staff was sooo helpful that stood out the most honestly I loved it I’ll book again definitely "
United States
Aliah
The price is HK$852
HK$1,340 total
includes taxes & fees
2 Mar - 3 Mar
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, (37 reviews)
"Many local restaurants near by. Christy's for breakfast was very good. "
United States
Benjamin H.
The price is HK$627
HK$1,408 total
includes taxes & fees
26 Feb - 27 Feb
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, (28 reviews)
"Fantastic experience from beginning to end! Loved every minute of my stay! "
United States
Jody U.
The price is HK$977
HK$1,978 total
includes taxes & fees
4 Mar - 5 Mar
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
Exterior

Family Stays: Middletown, CT

Family Stays: Middletown, CT
Middletown
10.0 out of 10, Exceptional, (21 reviews)
"A truly wonderful experience! The host and home were amazing and we’ll definitely be staying here again!"
United States
Harmony R.
The price is HK$978
HK$1,844 total
includes taxes & fees
2 Mar - 3 Mar
Family Stays: Middletown, CT
Exterior

Walk To Goodspeed Opera House!

Walk To Goodspeed Opera House!
East Haddam
9.4 out of 10, Exceptional, (34 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 HK$1,525
HK$2,453 total
includes taxes & fees
26 Feb - 27 Feb
Walk To Goodspeed Opera House!
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, (21 reviews)
"Enjoyed our stay - Highly recommend!"
United States
Mary S.
The price is HK$1,056
HK$2,099 total
includes taxes & fees
1 Mar - 2 Mar
The gardners Cottage 1 mile from long Island Sound - pet friendly
Dining

LONG-TERM Skiing, Tubing 30 mins away and the Ocean 5 mins!

LONG-TERM Skiing, Tubing 30 mins away and the Ocean 5 mins!
Clinton
10.0 out of 10, Exceptional, (4 reviews)
"Beautiful home in a quiet neighborhood. We greatly enjoyed staying at Glass House. "
United States
Elya D.
The price is HK$845
HK$3,852 total
includes taxes & fees
4 Mar - 5 Mar
LONG-TERM Skiing, Tubing 30 mins away and the Ocean 5 mins!
Interior

Conference Room Rental no sleeping arrangements

Conference Room Rental no sleeping arrangements
Main Street Historic District
The price is HK$5,632
HK$7,283 total
includes taxes & fees
26 Feb - 27 Feb
Conference Room Rental no sleeping arrangements
Property grounds

COZY Maple Tree Cabin - Situated on 6 private acres- Enjoy nature

COZY Maple Tree Cabin - Situated on 6 private acres- Enjoy nature
Killingworth
10.0 out of 10, Exceptional, (55 reviews)
"Amazing property, we loved everything about it, highly recommended, will stay again "
United States
Rick
The price is HK$3,519
HK$6,421 total
includes taxes & fees
27 Feb - 28 Feb
COZY Maple Tree Cabin - Situated on 6 private acres- Enjoy nature
Fridge, microwave, oven, stovetop

2BR Apartment Near Wesleyan 301

2BR Apartment Near Wesleyan 301
Washington Street Historic District
The price is HK$790
HK$2,184 total
includes taxes & fees
2 Mar - 3 Mar
2BR Apartment Near Wesleyan 301
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 HK$1,155
HK$1,680 total
includes taxes & fees
8 Mar - 9 Mar
Cozy Guest Suite in Historic Home
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
10.0 out of 10, Exceptional, (25 reviews)
"Wonderful house in a great location."
United States
Edward S.
The price is HK$4,691
HK$7,580 total
includes taxes & fees
13 Mar - 14 Mar
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
2 bedrooms, desk, iron/ironing board, travel cot

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 HK$1,057
HK$3,016 total
includes taxes & fees
26 Feb - 27 Feb
1st Floor Westbrook Anchor | 2 Queen Beds | EV Charger | Near Beach
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 HK$1,282
HK$4,212 total
includes taxes & fees
3 Mar - 4 Mar
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, (43 reviews)
"Great property, would stay here again."
United States
charles b.
The price is HK$1,789
HK$3,821 total
includes taxes & fees
1 Mar - 2 Mar
Driftwood Cottage @ Saybrook Point Marina, 2 King Beds
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 HK$1,407
HK$2,823 total
includes taxes & fees
26 Feb - 27 Feb
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 HK$790
HK$2,215 total
includes taxes & fees
10 Mar - 11 Mar
Private Apt in Middletown-Wesleyan 101
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 HK$1,330
HK$1,701 total
includes taxes & fees
26 Feb - 27 Feb
3-bedroom Unit in tranquil Middletown
1 bedroom, desk, iron/ironing board, travel cot

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$785
HK$2,311 total
includes taxes & fees
26 Feb - 27 Feb
Private 2nd-Floor Apt | 4 Mins to Beach | EV Charger & Parking Included
Dining

2BR Apartment Near Wesleyan 102

2BR Apartment Near Wesleyan 102
Washington Street Historic District
The price is HK$743
HK$2,168 total
includes taxes & fees
3 Mar - 4 Mar
2BR Apartment Near Wesleyan 102
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

Mohegan Sun

Mohegan Sun

10/10 Excellent
"Great experience!"
Joao 1-night trip
Posted 2 days ago
Mohegan Sun