Top 10 Airbnb Vacation Rentals In Connecticut, USA - Updated 2023

Sharon A.
Sharon A.  
| 5 min read

Connecticut, also known as the Nutmeg State, may be a small state, but its impact on the country’s politics, art, culture, and history can’t go unnoticed. Its mesmerizing beauty, starting from the East Coast Urban Centers to the breathtaking Bear Mountains, is a popular travel destination for all kinds of travelers seeking solitude. The traditional seaports, historic architecture, expansive farms, museums, casinos, and historic houses have more than enough to offer round-the-clock entertainment for any duration of travel. To get the most out of your trip, however, you need a solid itinerary, and this should include decent, comfortable and convenient accommodation. Check out our recommendations for the top Airbnb in Connecticut, USA, that are bound to make your nights comfortable so that you are full of energy the following day for more exploration of the region.

1. Waterfront studio with a private patio, Milford (from USD 169)

This is a beautifully designed studio apartment with a large private patio that boasts the breathtaking views of the Long Island Sounds. It comes with a spacious interior, featuring a queen bed, spacious seating area, a dining section with a dining table and chairs, a fully equipped kitchen, a private bath, a flat-screen TV, and a fireplace. The patio has sunbeds and chairs where you can lounge on while you watch the sunset and soak in the beautiful views above the waters. If you would love to explore around, Downtown Milford is only ten minutes away from the property.

Stayed at this property?
Milford, Connecticut, United States
54.27 km (33.8 mi) from Gillette Castle State Park
484 reviews   Superhost Wifi Available
ENTIRE RENTAL UNIT 1 Bed 2 Guests 1 Bedroom 1 Bathroom

Accommodates: 2

Top guest reviews
Amenities & Room:
we enjoyed the outside patio grilling sunset views indoor fireplace a beautiful kitchen and jets in the shower
the next day he purchased a system that boosted the wifi to every spot on the property
the bathroom was wonderfully designed as was the entire apartment
the view outside the apartment is fantastic the inside is comfy- intriguing decor
i walked out of my room right onto a beautiful large deck overlooking the ocean
everything was very clean
it's a beautiful clean apartment
the studio is immaculately clean and luxurious
luxurious impeccably clean great communication with the owner
the studio was truly beautiful clean and spacious
david is a wonderful host
david is an amazing host
david is an amazing host
lovely host with quick response time
david was a very gracious host
close to milford center and near lots of great places to eat
i was pleased with the location and price
i would highly recommend this location
it’s also a quick trip to the train station so you can ride to nyc with ease
property is super close to new haven area which makes it convenient for dining out
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2. Beautiful hideaway with wooded views, Guilford (from USD 250)

It is a beautiful winter getaway located right in the middle of the woods. It is private, secluded and comes with all the amenities you will need for comfort and convenience during your stay, including a towel warmer, heated floors in the bathroom, a fully equipped kitchen, and a spacious living room with large glass doors opening up to the beautiful patio. If you are looking for peace and tranquility, both during the day and at night, and in a place where the beach is just a few miles away, then this will make a great option for your accommodation in Connecticut.

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Guilford, Connecticut, United States
29.52 km (18.4 mi) from Gillette Castle State Park
443 reviews   Superhost Wifi Available
Entire guesthouse 1 Bed 2 Guests 1 Bedroom 1 Bathroom

Accommodates: 2

Top guest reviews
Amenities & Room:
the wifi worked very well
the property is gorgeous and the view from the living room is so relaxing
heated bathroom floor was a nice touch
we loved the heated floor (and towel rack ) in the bathroom - such a great touch
clean and stylish in a beautiful setting
very clean comfortable and easy communication with the hosts
this place is very clean and modern as well as comfortable
this place is beautifully kept impeccably clean and serenely quiet
the house looks modern very clean very cozy
they were great hosts
they were incredibly responsive and welcoming: really great hosts
great place and amazing hosts
our host gave us some good recommendations e
the host goes out of their way to make you feel comfortable
perfect location on connecticut coast
the place is very near guilford with good restaurants and cute shops
it’s close to many great restaurants and hiking trails
what a lovely lovely bnb the location is simply ideal
great place to relax and get away from the city
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3. Riverfront cottage with a front yard, Chester

The cottage sits on the banks of the Connecticut River in the old mill town of Chester. It features a living room fitted with a comfy couch, a dining area, and a fully equipped kitchen with all the essentials you may need to prepare a decent home meal. The bedroom has a queen-sized bed and a bathroom with a shower and tub. The property also features a beautiful private front yard, with the river flowing just a few meters away.

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Chester, Connecticut, United States
1.84 km (1.2 mi) from Gillette Castle State Park
417 reviews   Superhost Wifi Available
ENTIRE HOME 4 Beds 4 Guests 1 Bedroom 1 Bathroom

Accommodates: 4

Top guest reviews
Amenities & Room:
beautiful view and comfortable accommodations
breath taking views very comfortable homey atmosphere
the views were amazing and a super comfy bed
the cottage is very comfortable for 2-4 people
great location beautiful view well-equipped kitchen (nice outdoor grill)
the place is clean and has a charm that was great to enjoy
clean scenic and a good value
quiet comfortable clean and laid back
it was super clean and roomy for the two of us
private quiet clean comfy great views
claudia was a wonderful host
the hosts are kind and responsive and unobtrusive
hosts were gracious and responsive
claudia and gordon are kind and quickly responsive to questions
claudia was a responsive and helpful host
wonderful location on the river and near the village of chester
very close to the charming village of chester
a lovely location right on the connecticut river
the location is absolutely beautiful and tranquil
great location and cute cottage right on the ct river and close to the town of chester
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4. Private one-bedroom apartment with elegant furnishings, Portland (from USD 85)

It is a one-bedroom apartment, featuring a stylish design with elegant furnishing. It is spacious, with a comfy seating area fitted with a satellite TV, and a dining section with dining chairs and a table. The apartment also comes with a full kitchen with all the appliances you may need to prepare your meals. The bedroom has a queen-sized bed and a private bath with a sink and shower. The apartment is less than a 10-minutes’ drive from Downtown Middletown, Middlesex Hospital, and Wesleyan University.

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Portland, Connecticut, United States
24.92 km (15.5 mi) from Gillette Castle State Park
452 reviews   Superhost Wifi Available
ENTIRE RENTAL UNIT 1 Bed 3 Guests 1 Bedroom 1 Bathroom

Accommodates: 3

Top guest reviews
Amenities & Room:
lots of space air conditioned and great bed
the window a/c units worked very well
there was easy parking effective air conditioning and a plenty of space
comfortable and spacious one bedroom apartment style air bnb
the home was full of amenities such as toiletries hygiene products snacks breakfast food coffee and fresh fruit
very clean and quiet
very clean and bright
the beddings and towels are very clean and also smell very clean just like in 5-star hotels
an extremely clean and convenient place
the place is very clean and spacious
sara is a great host
great place and great host quick responses and offered any help we needed
great space and awesome host
sara is a great host definitely recommended
sara quickly responds all the questions and very helpful
perfect location for us with easy access to middletown and all of central ct; 20 minute drive to hartford
good location and easy to find
sara’s place is cute and modern
it is close to a grocery store and several great restaurants
nice location and good value for the space
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5. Renovated apartment with water views, New Haven (from USD 100)

The newly renovated one-bedroom apartment is located in a quiet and serene setting, with beautiful water views. It features new appliances and furniture, as well as a fully equipped kitchen to make the process of home meal preparation a breeze. It is comfy, welcoming, and in a location that offers great proximity to some of the best attractions in the city. Yale is only 15 minutes away by bus. The Marina and Anastasios Boat Café is also a few minutes’ walk for guests who don’t want to make it to downtown for dining.

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New Haven, Connecticut, United States
39.76 km (24.8 mi) from Gillette Castle State Park
459 reviews   Superhost Wifi Available
ENTIRE RENTAL UNIT 1 Bed 2 Guests 1 Bedroom 1 Bathroom

Accommodates: 2

Top guest reviews
Amenities & Room:
beautiful view and cozy apartment
parking amenities clean and comfortable rooms as well as a great lakefront view
artists writers and couples looking for cozy solitude with a view will love this place
sparkling clean modern apartment with an amazing outdoor space and water view only minutes from downtown new haven
ricardo's place is complete with everything you need for a comfortable new haven stay
super clean and fresh
very clean very friendly
very clean stylish and comfortable
apartment is very clean and inviting
great place it is clean and comfortable
richardo was a great host
beautiful place great host & very kind very welcoming & cozy
ricky is an excellent host
ricardo was a great host
and ricardo is a very friendly host who offers genuine hospitality
gorgeous location right on the water
great location to travel into downtown new haven
a lovely apartment in a great location
such a cute place and a wonderful stay
the location is amazing suite is a lot more fashionable and retro themed
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6. Lovely two-bedroom apartment in a quiet location, Glastonbury (from USD 110)

The apartment is located just a mile from the Connecticut River, and it is in a quiet location that is not only peaceful, but also calming to the mind, body, and soul. It has a very comfortable living room featuring comfy seating, and a flat-screen TV and free Wi-Fi for entertainment. The kitchen is fully equipped with all the appliances you may need to prepare home meals, and the bathroom is also well-stocked with fresh towels and free toiletries. From the property’s location, there are plenty of hiking areas, restaurants, and shops for any extras you may wish to have during your stay.

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Glastonbury, Connecticut, United States
28.63 km (17.8 mi) from Gillette Castle State Park
398 reviews   Wifi Available
ENTIRE RENTAL UNIT 2 Beds 5 Guests 2 Bedrooms 1 Bathroom

Accommodates: 5

Top guest reviews
Amenities & Room:
there’s one fan in the unit
the two beds and extra couch was perfect for the family of four
what the photos don’t show you are beautiful farm country an enormous outdoor space and the heated pool
lots of space and very comfortable beds the best air b&b experience i have had to date
i loved how there was a washer/dryer and a kitchen for me to use
clean cozy and spacious
spotless and very comfortable
clean quiet & comfortable
the apartment was very clean and comfortable
alice’s place was very clean and cozy
alice and tom were wonderful hosts
the host communicated very well with myself
alice is a gracious host and will quickly answer any questions you may have
awesome spot alice was a great host
worth every penny super nice host awesome awesome awesome
the location is so peaceful and central to the areas we visited
great location within walking distance of the elementary school playground
great value and location feels homey and comfortable
what a fabulous location and what super hosts
close to hartford as well and alice is very responsive
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7. Private oasis best for couples, Shelton (from USD 134)

It has been described as the ultimate couple’s getaway, and this is rightly so, owing to the range of luxurious amenities which it has and which most couples will be glad to have. It is a fully furnished one-bedroom apartment located right in the middle of the woods, giving it the peace and serenity most couples would wish for during their getaway. Notable features include a 60-inch smart TV with a soundbar, a home theater, a swimming pool, a hot tub, a full kitchen, comfy queen beds, a hot tub, and an outdoor leaving room with comfy seats and a fire pit.

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Shelton, Connecticut, United States
59.04 km (36.7 mi) from Gillette Castle State Park
311 reviews   Wifi Available
ENTIRE RENTAL UNIT 1 Bed 4 Guests 1 Bedroom 1 Bathroom

Accommodates: 4

Top guest reviews
Amenities & Room:
the pool and view were so appreciated
great place to stay stylish and comfortable with all the amenities you could need for a relaxing stay
we made good use of the beautiful pool and the beautiful views
the bed is very comfortable the ac was great they kept it cool and i loved that
we wanted to explore the town more but decided instead to enjoy the resort quality pool/hot tub area
very clean and quiet
the bathroom was clean and the shower was great
lovely place clean and enjoyable
the apartment is really beautiful clean and stress free
the hot tub is clean and kept super hot
the host was very polite and helpful
the hosts are easy and quick communicators
she also had tons of helpful recommendations
the host was great at giving advice on where to go and quick and responding
amazing hosts were accommodating and helpful
great location the house is just stunning
it’s a great location and lovely neighborhood to walk around
amazing place beautiful location and close to the town and local farms definitely recommend
definitely felt very safe at the location
great location for downtown and local breweries
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8. Lakeside cabin with a sauna, Voluntown (from USD 120)

The cabin has been nicknamed “Vinola” and it is a great choice for the nature enthusiast in need of ideal accommodation in Connecticut. The charming cabin sits gently on the shores of a lake and surrounded by tall, mature woods. It is decently furnished, with a comfortable sofa, a fully functional kitchen, a private bathroom with shower, and a front porch with two chairs and a table. With such a location, there are plenty of exciting outdoor opportunities here, including kayaking, hiking, fishing and swimming.

Stayed at this property?
Voluntown, Connecticut, United States
54.81 km (34.1 mi) from Gillette Castle State Park
638 reviews   Superhost Wifi Available
Entire cabin 6 Beds 6 Guests 1 Bedroom 1 Bathroom

Accommodates: 6

Top guest reviews
Amenities & Room:
we had two families (with small kids) in here and were quite comfortable
the cabin was beautiful and cozy and the sauna was the perfect touch for our relaxing night in
warm and cozy and always welcomed by some snacks
cabin was sparkling clean very cozy
the cabin was clean and well equipped
amazing little cabin it was very clean and welcoming
the cabin is thoughtfully decorated sparkling clean and wonderfully inviting
clean and lovely with so many things to do could not recommend it more
amazing place host went above and beyond
angela is a great host
i could tell that the host has made thoughtful touches
the host and her family are gracious and charming
angela and her family are wonderful hosts
a great family location by the lake
beautiful location and the sauna is just perfect
the location is ideal for anyone looking for a reprieve from city dwelling
a cozy cabin in a beautiful location
peaceful cabin that was comfortable near a beautiful lake and close to great local hiking spots
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9. Tiny house with forest views, Norwich (from USD 125)

This is a tiny cedar octagon house with electricity but no running water or plumbing. It is located right in the middle of a forest, surrounded by beautiful views and sounds of nature. It features a full-size bed, a table with two chairs for dining, a cabinet for storing camping essentials, and lamps with charging ports for more convenience. Upon arrival, instructions will be provided on how to use the propane heater and you will also be supplied with a trail map to help you find your way to the incredible adventures within the forest.

Stayed at this property?
Norwich, Connecticut, United States
26.51 km (16.5 mi) from Gillette Castle State Park
732 reviews   Superhost Wifi Available
Tiny home 0 Beds 2 Guests 1 Bedroom 0 Bathrooms

Accommodates: 2

Top guest reviews
Amenities & Room:
i would like to give extra credit though on this review to the shower
nancy and bert literally thought of every little detail to make your stay magical and comfortable
the outdoor shower is a nice touch and was hotter and stayed hot for a very long time
the space was super cute and cozy
it was warm and comfortable even in the winter (including the outhouse)
everything was extremely clean including the outdoor shower
quite cozy clean and comfortable
the place is all beautifully maintained and cleaned and marked out for trails
amazing one night was not enough clean friendly and fun
beautiful land and very cozy and clean room by the brook
bert and nancy are excellent hosts
great hosts who are very attentive
bert and nancy were amazing hosts
fabulous stay they were such kind hosts and went above and beyond
and the good energy the hosts project
this is such a special location
wonderful couple and wonderful location
nancy and bert created walking trails that were so cute
this place is perfect for a getaway nancy and bert were super helpful about explaining everything
nancy and bert have created such an amazing place to decompress from everything going on
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10. Historic Craftsman bungalow with a garden, Wallingford (from USD 81)

This is a historic Craftsman bungalow constructed in 1915, but still intact to provide you with a good accommodation experience in Connecticut. It features a spacious bedroom that comes with an en-suite bath. There’s also a fully equipped kitchen complete with a coffee maker, toaster, and fridge, and a spacious living room with a TV, dining and reading areas. The property has a beautiful front porch that leads to a well-maintained garden with furniture ideal for outdoor relaxation. From the bungalow, Downtown is less than 2.5 mi (4 km) away. Dining, shopping, and entertainment options are just a few minutes’ away from this property.

Stayed at this property?
Wallingford, Connecticut, United States
32.31 km (20.1 mi) from Gillette Castle State Park
471 reviews   Superhost Wifi Available
Entire guest suite 1 Bed 2 Guests 1 Bedroom 1 Bathroom

Accommodates: 2

Top guest reviews
Amenities & Room:
there were comfortable chairs in the sitting room and the bed was super comfy as well
apartment:floor to ceiling windows frames a beautiful view of the landscaping
the kitchen had more than just complimentary bottles of water
the bathroom is incredibly well equipped bed is super comfy and extra space just lovely
the huge mission-style bed was also extremely comfy
the cleanliness was immaculate and the bed very comfortable
super clean well-stocked awesome accommodations
super clean very relaxing environment
very comfortable clean and exceptionally appointed rental
i was spacious clean and very comfortable
hosts were very hospitable and kind
this is a charming home offered by equally charming hosts
hosts were very friendly and helpful
great place and great host
tracy was a wonderful host
conveniently located near restaurants shopping entertainment and major access roads
outstanding location and high end accommodations
great location and attention to detail
the location is great - there are plenty of restaurants and shopping nearby as well
it’s close to restaurants and a few stores if you need anything and was easy to find
Read more reviews

Enjoy comfortable accommodation in Connecticut

Don’t ruin your Connecticut experience by going for awful accommodation. Consider our recommendations of the top Airbnb in Connecticut, USA, that are safe, comfortable, and affordable, too.

Stayed at this property?
Any must-sees we missed? Tell us about them in the comments section or write a post here to help out fellow travelers!
Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.


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Sharon, also known as Shaz, resides in the vibrant City in the Sun. Her passion is to travel, immerse herself in diverse cultures, savor their cuisines, dance with the locals, and share her...Read more

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