Holiday rentals with outdoor seating in Bridgeport

Find and book unique Holiday Houses with Outdoor Seating on Airbnb

Top-rated Holiday Houses with Outdoor Seating in Bridgeport

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Guest favourite

Apartment in Milford

4.94 out of 5 average rating, 109 reviews

The Boathouse, private downtown Harborside suite

The Boathouse is a detached one bedroom studio apartment situated behind our home in the heart of Historic downtown Milford. Through a private entrance you will discover a thoughtfully furnished bedroom (queen bed & pull out couch), dining room, full kitchen & bath. It is ideally suited for a couple/small family looking for a memorable beachtown getaway. Walk, rent bikes/kayaks, shop, dine, enjoy art, music, or a day at the beach… our quintessential New England seaside town is sure to charm you!

21–28 Jun

$415 NZD per night

Guest favourite

Guest suite in Fairfield

4.93 out of 5 average rating, 112 reviews

Adorable private apt w/ W/D in lovely neighborhood

Enjoy a lovely experience at this centrally-located studio in-law apartment. It boasts a newly renovated kitchen and bath, king bed with brand new mattress, pull out full size sofa, ample closet space and more. The eat-in kitchen has all you need to feel right at home. The apartment is located adjacent to a nice residential house, but is fully private with your own front and back entrances. There are also no stairs, making it easily accessible. It’s located in a wonderful neighbor in Fairfield.

2–9 Sep

$230 NZD per night

Guest favourite

Apartment in Milford

4.97 out of 5 average rating, 512 reviews

Water front studio apartment with fireplace.

This is a beautifully appointed studio apartment located off the patio level of a water front home. Guests enjoy a large private patio over looking gorgeous sweeping views of Long Island Sound. A private entrance and off street parking. The amazing views and amenities make this space the perfect romantic getaway! Close to I95 and Metro North railroad. Ten minutes to great dining in downtown Milford. A true waterfront oasis! Come and experience this beautiful retreat! You won't be disappointed!

18–25 Oct

$400 NZD per night

Guest favourite

Home in Milford

4.98 out of 5 average rating, 153 reviews

Designer Beach Retreat on Exclusive Cedar Beach

Welcome to your own slice of heaven! Enjoy dinner in your Chef's kitchen while watching one of the most radiant sunsets you will ever see. Stunning views from the private rear deck or snuggled on the couch inside the living room. Wade into Long Island Sound with semi-private beach access 250 feet away. The property is 5 doors down from the CT Audubon Society, known for its epic views and wildlife watching. The sunrises & sunsets are beautiful! 15 minutes to Yale. We can't wait to host you!

8–15 Oct

$655 NZD per night

Superhost

Apartment in Bridgeport

4.89 out of 5 average rating, 122 reviews

The Charles 456 KingBeds FastWIFI free2park+office

Experience a peaceful escape in this charming two-bedroom apartment. With spacious rooms featuring King-sized beds and flat-screen TVs, you'll have all the comfort and luxury you need. The modern bathroom has everything you need to feel at home, and the inviting living room with a large TV provides the perfect space to relax. The well-stocked kitchen, complete with butcher block counters and a sleek stainless-steel fridge, makes it easy to cook and enjoy a meal. Book your stay today.

1–8 Feb

$323 NZD per night

Guest favourite

Apartment in Redding

4.94 out of 5 average rating, 459 reviews

Huckleberry Quarters, the Cozy Redding Retreat.

Now is the time to book your spring getaway to the Huckleberry Quarters, a totally renovated (2015) studio apartment with full bathroom in a secluded, 1918 farm house. A nature lover's retreat within hiking distance of the Saugatuck reservoir and the Centennial Watershed Forest. Private entrance with all the amenities; internet, access to laundry. A Perfect weekend getaway or writing/artist space. Easy access to Merritt Parkway, trains, local eateries, parks.

12–19 Oct

$273 NZD per night

Guest favourite

Apartment in Brookfield

4.94 out of 5 average rating, 186 reviews

Peaceful apartment on 3.5 acres w/ Artist studio.

Welcome to our cozy apartment! This fully enclosed apartment is attached to our main house on a beautiful 3.5-acre property in Brookfield. Enjoy a kitchen, comfortable living and bedroom area, and a clean bathroom. Guests have access to a shared 32 ft, 10 ft deep pool, artist studio, pool table,, garden, fire space, and outdoor seating. We provide a guidebook for your convenience. Book now and experience a perfect blend of comfort, creativity, and relaxation.

12–19 Apr

$244 NZD per night

Guest favourite

Guest suite in Fairfield

4.94 out of 5 average rating, 361 reviews

Private Studio Apartment; Kitchen; Fully Furnished

This 625 sqft fully furnished studio apartment has its own private entrance and sleeps 2-3 with a queen bed and Murphy bed. Other than outside, there is no contact with other people (hosts, other guests, etc) possible unless the guest allows such. The unit consists of a living room, dining space (breakfast basics provided), kitchen, full bathroom/laundry. Walk to Fairfield University; an easy train ride to NYC. Please let us know how many beds you need.

30 Jan – 6 Feb

$256 NZD per night

Superhost

Loft in Bridgeport

4.86 out of 5 average rating, 174 reviews

Cozy Loft in beautiful St. Mary's by the Sea

Renovated cozy loft in beautiful St. Mary's by The Sea in Black Rock. Walking distance to award winning restaurants. Easy access to NYC/New Haven Metro North transit. Perfect for a weekend at the beach. Property includes 1 bed and a 78” sofa. Fully equipped kitchen with all major appliances, WiFi, & large TV. ***Please note that the ceilings are angled so taller guests (over 5’ 8”) might have to bend in certain parts of the loft.

3–10 Feb

$313 NZD per night

Guest favourite

Apartment in West Haven

4.9 out of 5 average rating, 423 reviews

! ! ! entire apartment close to the beach ! !

Come and experience West Haven and the Long Island Sound in this nice and cozy apartment close to the beach. Our apartment is complete with a full-size kitchen, bathroom, cable TV, laundry room, fresh linens, towels, air conditioning, wide driveway, and free WiFi. We will provide some FREE complimentary snacks. This apartment is ideal for single travelers, couples, and can accommodate up to three people (adults only).

5–12 Feb

$195 NZD per night

Guest favourite

Guest suite in New Haven

4.99 out of 5 average rating, 157 reviews

Cozy cottage in historic neighborhood

Housed in a 100-year-old building nestled between the Victorian houses in New Haven's historic City Point neighborhood, once the center of New England's oyster trade, our cottage is a two-block walk from the marina (and its award-winning restaurant), a 10 minute-drive from the West Haven beaches and a few minutes' drive to Yale.

27 May – 3 Jun

$294 NZD per night

Guest favourite

Home in Milford

4.99 out of 5 average rating, 231 reviews

The Daydreamer -Walk to Walnut Beach, Pet Friendly

Newly remodeled and designed, come enjoy your cozy bungalow just 0.2 miles from beautiful Walnut Beach & boardwalk. Less than 1 minute to The Tyde wedding venue. 10 miles from Yale, Fairfield U & Sacred Heart U. 10 minutes from the Total Mortgage arena. Located on a private one way street, less than 5 minutes to I95

7–14 Mar

$472 NZD per night