Apartment holiday rentals in Bridgeport

Downtown Elegant Stay By Yale • Rooftop • Gym

Come and stay at this luxury, modern one-bedroom apartment just steps away from Yale! With Broadway just around the corner and some of New Haven’s best Pizza a stone’s throw away you’d be hard-pressed to find a better location for your stay. Enjoy cooking up a nice dinner at home one night using the fully-equipped kitchen provided. Spend the evening on the rooftop terrace watching the sunset over the city skyline before tucking in for the night. Use the downstairs gym for a morning workout.

Location · Value · Amenities

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!

Family · Value · Hot tub

Bright 1 BR Apt Steps From Yale

Enjoy a bright and cozy 1 bedroom apartment just 2 blocks from the Yale campus and The Shops at Yale. Located in a 3 unit brick building, designated as a property on The National Register of Historic Places, this small renovated 2nd floor apartment maintains the characteristics of the building's original design, while providing all amenities needed for a comfortable stay. Convenient free off street parking provided. Great shops, restaurants, nightlife, and museums can all be accessed by foot.

Value · Location · Backyard

The Pond Mill Retreat w/ 2 Bdrms & Pool

Catch up on a little work or simply unwind. Everything is waiting for you in this cozy, yet functional space surrounded by a beautiful wooded area with pond. Your private entrance accommodations include a finished, walk-out lower-level apartment (~730 sq ft) containing thoughtfully appointed bedrooms, living room, kitchen, and full bathroom. Experience solitude while enjoying the convenience to Rt 15, I-95, & Boston Post Rd destinations. And if you require assistance, we live right upstairs.

Value · Location · Hiking

The Pearl, New Haven

Amazing hidden luxury experience along the Quinnipiac River in a historic mid-19th century property. Enjoy the scenic river and sunset views, soak in our stunner claw-foot tub, recharge in the sunlit living room, work in the dining alcove, or relax by the bay windows with your favorite drink. NO KITCHEN, but we have a coffee maker, tea kettle, toaster oven, microwave, fridge, plates, and cutlery. We are 15 mins drive from Yale, 2 mins walk to the downtown bus, and easy cycling downtown.

Location · Value · Air conditioning

Luxurious 3BR Apartment w/ Parking & Gym

Our prime location meets modern elegance. This three-bedroom spacious apartment is designed for comfort, convenience, and sophistication in the heart of a dynamic urban community. Whether planning a quiet night in or a lively evening downtown, Hyatus amenities elevate your living experience. º Rooftop Sky Lounge with an outdoor TV º Screening area º Cabanas º Billiards º Bocce courts º Fireside lounge º Co-working space featuring private work pods º Meeting rooms º Cappuccino Bar

Family · Value · Comfort

The Farmhouse Estate Apartment

Perfect for families & groups! This 3 bed & 1 bath unit is located on the 1st floor of a turn-of-the-century Farmhouse outfitted with modern amenities. The unit has been specifically designed for Airbnb use and has a boutique hotel feel. Enjoy hardwood floors, Queen memory foam mattresses, high ceilings, keypad door lock (no keys needed), central air, private deck & beautiful views of a 1 acre yard with adjacent apple orchard. No parties or events allowed.

Value · Location · Cleanliness

Cozy & Private Apartment Near the Ocean

Relax by the Shore in Cozy Comfort 🌊 Unwind in our charming West Haven apartment, just minutes from the beach, bird sanctuary and the scenic Long Island Sound. This inviting space features a full kitchen, private bathroom, cable TV, fresh linens and towels, air conditioning, free WiFi, and a spacious driveway for easy parking. Perfect for solo travelers or couples, and comfortably fits up to 3 adults. Your beachside escape awaits!

Family · Value · Getting around

Sunny Fairfield Studio Apartment

Enjoy this sunny, newly-renovated, modern Fairfield studio apartment, located in the carriage building of a historic early 1900's house. Great for an individual, couple, or family. Well situated, a short drive to Sacred Heart & Fairfield Universities, downtown Fairfield and the beach, Silverman's Farm and other Easton farms for apple picking, petting zoos, and the like, and Fairfield Metro Station for a 1 hour train ride to NYC.

Family · Location · Heating

Stylish Sheek Loft Ricport Studio 2, Downtown

Please note location and area before booking!!! (DONT BOOK if you don’t know it’s loud and busy) Conveniently located Downtown in the city of Bridgeport. Feel free to light a fire🔥. Unique hand tinted windows provides the space with an open feel although it is a small space. Queen size bed, fireplace, and aesthetics sets this apartment apart from any rental you can find. *pet fee for pets. Please let me know in advance.

Value · Location · Condition

Cozy 2 Bedroom rental on Elm…

This special place is close to everything, making it easy to plan your visit. It’s in the city and close to just about all of your wants and needs. Lots if fine dining, Universities and fun shops that are a must see. Also conveniently located so you don’t need a car to get around. I’m also very glad to help with any questions, or if you just need suggestions on places to go or things to do. Hope to see you soon.

Value · Family · Quiet

Soaking Tub Retreat | Cozy Luxe Stay Near Yale

Relax in this peaceful retreat just 10 minutes from downtown New Haven and Yale. Ideal for solo travelers or anyone seeking a quiet escape. Enjoy the deep soaking tub, calming decor, fast Wi-Fi, and a serene space to recharge. No parties—just peace, comfort, and good vibes. This is a calm, intentional space for peaceful stays only. We welcome guests who appreciate good energy and quiet rest.

Value · Location · Beach