7 Mind-Blowing Airbnbs For The Ultimate Connecticut Staycation

With so much stunning scenery and slick cities like New Haven, it’s never a bad time for a Connecticut staycation. The state has lots to do and see, as well as some world-class restaurants.

These locations are all high-end Airbnbs which are ideal for large groups, families or a couple’s getaway. The best part is that once you divide the cost of the house between a group, it works out as a super affordable alternative to hotels and resorts.

All you have to do now is round up some friends and get ready to enjoy the ultimate Connecticut staycation in one of these beautiful Airbnbs…

Best Airbnbs in Connecticut

1. Luxury Getaway Oasis- Avon

This Luxury 10,000 sq ft home in the heart of Avon is the perfect place to relax & unwind! Finished basement with bar, billiards, home theater & gym. A recreation room for gaming, foosball & air hockey. Kids playroom full of games & toys! The ideal escape for a family or group of friends.

If you like to cook, this home comes with a chef’s kitchen with a butler’s pantry. For the colder nights, snuggle up to one of their 5 fireplaces! This house sleeps up to 12 guests with 5 en-suite bedrooms and His & her home offices. Backyard has an oasis-like pool & spa area, patios, grill, fire pit, lots of seating.

The nightly price for this luxurious home is $1,500.

2. Hilltop Mystic Mansion- Stonington

The Hill Top House is the perfect place for families and friends to get together. Over 5,000 square foot, and sleeping up to 14 guest, it’s ideal for a large group. The house also offers a separate apartment with a full kitchen and bath.

Situated on a quiet and peaceful two acres of land and located only two miles from downtown Mystic, experience the best of both worlds with this home. Sip on a glass of wine and enjoy the sunset looking over the mountains in the backyard. The nightly cost for this beautiful home is $875.

3. Country Estate- Sharon

Located in a very natural private setting surrounded by woods, fields, and gardens with a large back yard in the middle of 26 acres and just two hours north of New York City. Escape from the city in this stunning estate.

There are two great outdoor eating areas/patios available in warmer months and the large Webber Grill can be used year-round. The grounds can accommodate outdoor games such as croquet, badminton, horseshoes and various ball games. This beautiful home has 5 bedrooms, sleeps 10, is pet friendly, and perfect for smaller events. The nightly rate for this home is $700.

4. The French Chateau- Waterford

This 1920s French Chateau will make you feel as if you’ve been transported to France.  The house comes with a private beach and dock, guests are free to use the kayaks, paddleboard, and windsurfer. The house also comes with an indoor gym so you don’t have to leave the house to get some exercise!

With stunning views of the Niantic River from every bedroom, all of the 6 bedrooms have adjoining bathrooms. This home sleeps up to 12 guests and it will cost you $1100 per night.

5. Breathtaking Waterfront Home- Stonington

Located on a peninsula overlooking Fishers Island Sound, this property is in a world of its own. Situated above the shoreline on more than 8 acres, the grounds are spectacular with 600 feet of curving sandy beach and a 450-foot breakwater pier with dock!

On the grounds, you’ll find a saltwater pool, secret garden, tennis court, 30′ by 60′ ocean pool, hot tub, and sandy beach! This 2,000 square foot Guest House offers 3 bedrooms, 3 full bathrooms, and has a large living room with fireplace, dining area, and full kitchen. The cost for this home is $2,000 per night and sleeps up to 5 guests.

6. Silvermine Serenity- Norwalk

Nestled in the Heart of Silvermine, steps from Gray Barns Mercantile. New England downtown is 10 minutes away. There’s plenty to do without leaving this home, simply relax in your backyard oasis: plunge pool & beach overlooking Silvermine river &Waterfall. The property also includes a Writers Cottage for those looking for extra solitude.

In the downstairs, you’ll find the Great Barn Room which comes with a stocked (Complimentary) refrigerator with sparkling water and assorted beer, where you’ll enjoy the 4K TV, Apple TV, Keyboard w/microphone and speakers, and a second dining area. Enjoy a roaring fire in winter, or open the screen dutch doors for a spring breeze & listen to the waterfall.

Connecticut Staycation

7. Beachfront House On Private Beach- Milford

This beautiful and spacious 3600 sq ft is home to one of Milford’s most coveted waterfront locations. A private sandy beach, a large waterside entertaining area set beautifully on a sleepy side street. Boasting spectacular views of Long Island Sound and Charles Island. Walking distance to downtown Milford.

Connecticut Staycation

You won’t find a better location if you’re looking to relax on a beach for a week. Having a beach as your front yard is as cool as it gets! The house is spacious. This home can accommodate up to 8 guests and will cost you up to $1,300 per night.

Connecticut Staycation

Planning on spending some time in the state? You should check out the best road trips in Connecticut here.

Big 7 Travel Team