Middletown Holiday Rentals

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Check prices for these dates

In two weeks
13 Mar - 15 Mar
In two months
24 Apr - 26 Apr
In three months
22 May - 24 May
In four months
19 Jun - 21 Jun

Our top choices for Middletown holiday rentals

Property grounds

#24 *Serenity* A Lakefront Cottage Retreat

#24 *Serenity* A Lakefront Cottage Retreat
Middletown
9.8 out of 10, Exceptional, (21 reviews)
"It was our 3rd time staying and everything was as expected. New updates to the bathroom were nice surprise. Thanks again for a lovely stay while we visited our daughter at Wesleyan. "
United States
Robb F.
#24 *Serenity* A Lakefront Cottage Retreat
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
Exterior

Family Stays: Middletown, CT

Family Stays: Middletown, CT
Middletown
10.0 out of 10, Exceptional, (22 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$900
HK$1,762 total
includes taxes & fees
16 Mar - 17 Mar
Family Stays: Middletown, CT
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 HK$1,111
HK$2,991 total
includes taxes & fees
3 Mar - 4 Mar
#29 - Modern 5 Bedroom/2 Bath
Fridge, microwave, oven, stovetop

2BR Apartment Near Wesleyan 301

2BR Apartment Near Wesleyan 301
Washington Street Historic District
The price is HK$711
HK$2,124 total
includes taxes & fees
3 Mar - 4 Mar
2BR Apartment Near Wesleyan 301
Dining

2BR Apartment Near Wesleyan 102

2BR Apartment Near Wesleyan 102
Washington Street Historic District
The price is HK$704
HK$2,101 total
includes taxes & fees
8 Mar - 9 Mar
2BR Apartment Near Wesleyan 102
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$1,721
HK$2,222 total
includes taxes & fees
3 Mar - 4 Mar
3-bedroom Unit in tranquil Middletown
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$821
HK$2,267 total
includes taxes & fees
17 Mar - 18 Mar
Private Apt in Middletown-Wesleyan 101
View from property

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, (121 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$853
HK$1,341 total
includes taxes & fees
3 Mar - 4 Mar
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
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 gardners Cottage 1 mile from long Island Sound - pet friendly
Interior

Gardner Lake 2 Queen/1King/2 Bath/Laundry- Private

Gardner Lake 2 Queen/1King/2 Bath/Laundry- Private
Salem
10.0 out of 10, Exceptional, (6 reviews)
"Place is nice would stay again "
United States
nic
The price is HK$987
HK$3,131 total
includes taxes & fees
3 Mar - 4 Mar
Gardner Lake 2 Queen/1King/2 Bath/Laundry- Private
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$814
HK$1,542 total
includes taxes & fees
5 Mar - 6 Mar
Walk To Goodspeed Opera House!
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$3,520
HK$6,417 total
includes taxes & fees
3 Mar - 4 Mar
COZY Maple Tree Cabin - Situated on 6 private acres- Enjoy nature
Smart TV

#23 *COMFORT & LUXURY* 3 BR/2 BA House

#23 *COMFORT & LUXURY* 3 BR/2 BA House
Southington
9.8 out of 10, Exceptional, (8 reviews)
"Place was just as advertised. It was clean, comfy, nice neighborhood. Check in and out was easy with no issues. "
United States
Ryan A.
The price is HK$1,122
HK$2,628 total
includes taxes & fees
3 Mar - 4 Mar
#23 *COMFORT & LUXURY* 3 BR/2 BA House
TV

Once the old Schools house now a newly furnished Apartment

Once the old Schools house now a newly furnished Apartment
Wallingford Center
9.0 out of 10, Wonderful, (13 reviews)
"Excellent option for a short stay near the heart of it all in Wallingford."
United States
Jeanette W.
The price is HK$990
HK$2,366 total
includes taxes & fees
3 Mar - 4 Mar
Once the old Schools house now a newly furnished Apartment
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$739
HK$1,538 total
includes taxes & fees
4 Mar - 5 Mar
1-bedroom cottage with Grove Beach 🏖️ access.
Marina

Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.

Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.
Fair Haven
9.6 out of 10, Exceptional, (15 reviews)
"Had a really nice stay, enjoyed this open airy space with comfortable beds and beautiful light with a view of the river. Very nice time, would stay again."
United States
Brian B.
The price is HK$1,322
HK$2,506 total
includes taxes & fees
3 Mar - 4 Mar
Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.
Interior

Modern & Cozy Cape | 4 Bedroom House | Central Location

Modern & Cozy Cape | 4 Bedroom House | Central Location
Manchester Center
10.0 out of 10, Exceptional, (5 reviews)
"This house was perfect for the 4 of us. We all had our own bedroom and shared the bath. It’s very clean and close to everywhere we were going! The home is modern and the beds were comfy! I would stay there again. Great home! "
United States
Lorie D.
The price is HK$947
HK$2,215 total
includes taxes & fees
3 Mar - 4 Mar
Modern & Cozy Cape | 4 Bedroom House | Central Location
Exterior

All New 1BR with tons of Charm

All New 1BR with tons of Charm
Wallingford Center
9.8 out of 10, Exceptional, (8 reviews)
"Charming, unique, and very comfortable. Would surely stay again. "
United States
David S.
The price is HK$990
HK$2,366 total
includes taxes & fees
3 Mar - 4 Mar
All New 1BR with tons of Charm
Smart TV

Modern ~ 3 Bedroom House ~ Sleeps 8 ~ 11 mins to Hartford

Modern ~ 3 Bedroom House ~ Sleeps 8 ~ 11 mins to Hartford
Manchester
9.6 out of 10, Exceptional, (19 reviews)
"House was great & close to where we needed to be. "
United States
Erica M.
The price is HK$931
HK$2,158 total
includes taxes & fees
9 Mar - 10 Mar
Modern ~ 3 Bedroom House ~ Sleeps 8 ~ 11 mins to Hartford
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 Middletown Hotel Reviews

Holiday Inn Express Southington by IHG

Holiday Inn Express Southington by IHG

10/10 Excellent
"Easy check in, rooms clean, "
Kathleen 2-night trip
Posted 3 days ago
Holiday Inn Express Southington by IHG

Find out more about Middletown

Search for holiday rentals in Middletown on Expedia! You can easily find your home rentals, villas, holiday apartments in Middletown using one of the methods below:

  • View our selection of featured holiday rentals in Middletown
  • Use the map to find apartments and other holiday homes in the Middletown neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Middletown while they last

Look no further and take a look at our great range of rental properties in Middletown!

Frequently asked questions

Are there holiday rentals in Middletown?

Yes, there are holiday rentals in Middletown close to Kidcity Children's Museum, or you can select a more secluded option if you're looking for a relaxing stay. Middletown is known for its entertainment choices and festivals. Make sure you have time to check out the basketball games and university setting during your trip.

What are some of the best holiday rentals that Middletown has to offer?

A spacious TREETOPS Reunion/ Retreat/Event venue! Sleeps 10-12. Seasonal POOL!: This holiday home rental outside of Middletown is located in the city centre, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a balcony, a garden and a selection of books so that you can immerse yourself in your holiday.

How many holiday rentals are there in Middletown?

With 11 Expedia holiday rentals, you're guaranteed to find just the right place for your Middletown stay.

What’s there to see and do in Middletown?

Family-friendly attractions include Kidcity Children's Museum and Van Vleck Observatory, whereas Connecticut River and General Mansfield House are a couple of great spots to enjoy the outdoors. Other places in town to visit include Wadsworth Mansion and Middletown Nature Gardens.

What’s a holiday rental in Middletown like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Middletown. Holiday rentals feature amenities like laundry facilities and kitchens so you'll feel right at home. If you're concerned about a sanitised environment, a holiday rental can offer a sense of seclusion away from public hotel lifts and busy concierge desks while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive choice for family trips.