Middlesex County Vacation Rentals

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Check prices for these dates

Next weekend
Aug 22 - Aug 24
In two weeks
Aug 29 - Aug 31
In one month
Sep 12 - Sep 14
In two months
Oct 10 - Oct 12

Top Cities in Middlesex County

Vacation HomesVacation Homes

Middletown

Middletown

Featured Vacation Homes in Middlesex County

Thames River Retreat · CT College+Casinos+USCGA
Terrace/patio

Thames River Retreat · CT College+Casinos+USCGA

10.0 out of 10, Exceptional, (6)
"We found this home a perfect combination of being able to get away but also convenient to restaurants, stores, and activities. The view could not be beat and the house was clean and comfortable."
The price is CA $196
CA $715 total
includes taxes & fees
Aug 13 - Aug 14
Thames River Retreat · CT College+Casinos+USCGA
Cozy 2 bedroom home located minutes from downtown
Interior

Cozy 2 bedroom home located minutes from downtown

9.6 out of 10, Exceptional, (29)
"Perfect stay for the Yale-Harvard game. "
Cozy 2 bedroom home located minutes from downtown
NORTHFORK COTTAGE with POOL & HOT TUB - thru Columbus day
Outdoor spa tub

NORTHFORK COTTAGE with POOL & HOT TUB - thru Columbus day

4.0 star property
9.6 out of 10, Exceptional, (133)
"Loved our stay and will be back"
NORTHFORK COTTAGE with POOL & HOT TUB - thru Columbus day
Regency Inn and Suites - Non Smoking King
Dining

Regency Inn and Suites - Non Smoking King

8.0 out of 10, Very good, (3)
"Desk clerk was wonderful. Made sure my stay was everything that I needed."
The price is CA $120
CA $166 total
includes taxes & fees
Aug 12 - Aug 13
Regency Inn and Suites - Non Smoking King
Waterfront 3-bedroom house less an 1 mile to Foxwoods and Great Wolf Lodge
Property grounds

Waterfront 3-bedroom house less an 1 mile to Foxwoods and Great Wolf Lodge

7.6 out of 10, Good, (7)
Waterfront 3-bedroom house less an 1 mile to Foxwoods and Great Wolf Lodge
Cozy 3 bedroom minutes from Yale and the beach
Private kitchen

Cozy 3 bedroom minutes from Yale and the beach

7.4 out of 10, Good, (3)
"The inside was very clean, the back patio/garden area is cute, but the pool was green by day two. Overall we enjoyed our time here"
Cozy 3 bedroom minutes from Yale and the beach
Downtown Mystic Home Private Driveway Fenced in Yard Discounted longer stays
Terrace/patio

Downtown Mystic Home Private Driveway Fenced in Yard Discounted longer stays

10.0 out of 10, Exceptional, (103)
"A sweet cheerful place near the heart of mystic. We stayed for a week and found kitchen to be well equipped, house clean, comfortable, and conveniently located. "
Downtown Mystic Home Private Driveway Fenced in Yard Discounted longer stays
Beach Ready 3-bdrm house, Short Walk to Private Beach and Park, Lots of Parking
Beach nearby, sun loungers, beach towels

Beach Ready 3-bdrm house, Short Walk to Private Beach and Park, Lots of Parking

10.0 out of 10, Exceptional, (39)
"Very clean well kept property near beach - host very welcoming and receptive. Enjoyed our stay!"
Beach Ready 3-bdrm house, Short Walk to Private Beach and Park, Lots of Parking
The Cooper-Burke House
Beach nearby, beach towels

The Cooper-Burke House

10.0 out of 10, Exceptional, (27)
"Nice location and house "
The Cooper-Burke House
Another rental season is coming up.
Outdoor pool

Another rental season is coming up.

10.0 out of 10, Exceptional, (19)
"Absolutely beautiful home with everything you need for an enjoyable vacation. The host was a pleasure to work with making sure we were comfortable with our accommodations. Definitely a great place to stay. "
Another rental season is coming up.
Grammy's Lake House w/ Private Waterfront Access
Interior

Grammy's Lake House w/ Private Waterfront Access

9.4 out of 10, Exceptional, (13)
"Very comfortable rockers and Adirondack chairs make it easy to relax and enjoy the lake view. Our bed was comfortable, and Nile supplied all we needed with linens and soaps. We appreciated all the space and large dining table. Lake is beautiful. Very enjoyable stay. Exceptional communication with our host. "
Grammy's Lake House w/ Private Waterfront Access
Beautifully Restored 1890’s House in beautiful & picturesque downtown Mystic.
Exterior

Beautifully Restored 1890’s House in beautiful & picturesque downtown Mystic.

10.0 out of 10, Exceptional, (49)
"Amazing home away from home. Very clean and walkable. It was a perfect girls trip weekend "
The price is CA $550
CA $1,041 total
includes taxes & fees
Sep 7 - Sep 8
Beautifully Restored 1890’s House in beautiful & picturesque downtown Mystic.
Cozy Bungalow Just Minutes from Mystic, Westerly Beaches, Boating and Casinos! by RedAwning
Exterior

Cozy Bungalow Just Minutes from Mystic, Westerly Beaches, Boating and Casinos! by RedAwning

9.8 out of 10, Exceptional, (30)
"Great place to stay convenient to Mystic and Mohegan Sun with lots of outdoor space for a pet"
Cozy Bungalow Just Minutes from Mystic, Westerly Beaches, Boating and Casinos! by RedAwning
Work and Play Special! Extended Stay Discount
Outdoor pool, a heated pool

Work and Play Special! Extended Stay Discount

10.0 out of 10, Exceptional, (48)
"We had a lovely time at Cottage Green. Ingrid was a lovely owner and was very easy to communicate with!"
The price is CA $1,242
CA $2,146 total
includes taxes & fees
Sep 4 - Sep 5
Work and Play Special! Extended Stay Discount
The SandPiper
Terrace/patio

The SandPiper

9.8 out of 10, Exceptional, (24)
"My friends and I stayed here for a night after a wedding. It was the perfect place to stay after a long day. Host was kind and helpful with anything I needed! "
The SandPiper
Charming 2-bedroom house in marvelous Montville with WiFi, AC
Outdoor dining

Charming 2-bedroom house in marvelous Montville with WiFi, AC

9.0 out of 10, Wonderful, (2)
"Perfect!"
Charming 2-bedroom house in marvelous Montville with WiFi, AC
American Beech in Greenport - Petite King Room 7
Terrace/patio

American Beech in Greenport - Petite King Room 7

8.8 out of 10, Excellent, (3)
"We thoroughly enjoyed our stay!"
The price is CA $329
CA $492 total
includes taxes & fees
Aug 13 - Aug 14
American Beech in Greenport - Petite King Room 7
Beachfront Bliss , Inviting 3 bedroom + loft at Hawks Nest Beach!
On the beach

Beachfront Bliss , Inviting 3 bedroom + loft at Hawks Nest Beach!

4.8 out of 10, (3)
"Overall, my girlfriends and I had a good stay at this accommodation. Transparently, there were some hiccups in communication between the property manager and I in the week leading up to our trip that were not clearly stated in the home's description prior to us booking our stay, however, I felt that they were able to address my concerns and came up with solutions that felt satisfactory to my group and I. The property manager was overall understanding and receptive to my feedback through our...
Beachfront Bliss , Inviting 3 bedroom + loft at Hawks Nest Beach!
Pool/5 min walk to Beach/Restaurants/Museums- Village House w/backyard
Fridge, microwave, oven, stovetop

Pool/5 min walk to Beach/Restaurants/Museums- Village House w/backyard

4.0 star property
10.0 out of 10, Exceptional, (6)
"This place is an absolute gem. Four big bedrooms, a brand new kitchen and washer/dryer, lovely renovated interior, and huge fluffy towels in excess! A huge backyard with plenty of toys for little ones and a big patio table and chairs to enjoy amazing grilled dinners from the new gas BBQ grill was a huge plus. Also lots of beach chairs, beach towels, umbrella available for use! The owner was extremely communicative, thoughtful, and an excellent host. This house is on a QUIET street in busy Sag...
Pool/5 min walk to Beach/Restaurants/Museums- Village House w/backyard
Beach Front Arts & Crafts House With Gorgeous Views Of The Sound
On the beach, sun loungers, beach towels

Beach Front Arts & Crafts House With Gorgeous Views Of The Sound

10.0 out of 10, Exceptional, (122)
"Beautiful historic home, views of the Sound, pleasant walking neighborhood."
Beach Front Arts & Crafts House With Gorgeous Views Of The Sound
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

Omni New Haven Hotel at Yale

Omni New Haven Hotel at Yale

10/10 Excellent
"Great hotel near Yale with friendly staff "
Roger 2-night trip
Posted 1 day ago
Omni New Haven Hotel at Yale