Holiday rentals in Derby

4.73 out of 5 average rating, 494 reviews

Guest suite in Ansonia

Private Inn

Private(not shared) self check-in, clean, quiet, safe, and free off street parking on a cul de sac road. The suite is 600sq your own private bathroom, backyard, and number keypad for your convenience to enter/exit into the suite at will, there is high speed Wi-Fi, HD cable tv, Kcup machine, heat/ac (indoor fireplace) also a firepit outsde ,rubber track and tennis courts literally in the back yard. 5miles away from Yale/nh and 5mins to Griffen Hospital and major highways great local restaurants

4.98 out of 5 average rating, 104 reviews

Flat in Milford

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.

4.95 out of 5 average rating, 372 reviews

Flat in New Haven

Luxury Apt with Parking and Gym | Downtown at Yale

Nestled in the heart of New Haven’s historic downtown, our designer home is part of the city’s most prestigious new luxury complex, renowned for its unmatched amenities and design. Highlights: • Prime location just steps from Yale University • Immaculately cleaned before every stay • Complimentary coffee, plush linens, and premium toiletries • 24/7 state-of-the-art fitness center • Expansive rooftop terrace with grills and chic lounges • Over 700 sqft of bright and sophisticated living space

4.76 out of 5 average rating, 25 reviews

Flat in Monroe

Charming 1-Bedroom duplex apartment in Monroe

Welcome to Your Home Away from Home! Escape to our cozy 1-bedroom apartment nestled in a private setting in Monroe. Perfect for couples, solo travelers, or small families, this tranquil retreat offers all the comforts you need for a relaxing stay: Spacious Bedroom, Fully Equipped Kitchen, Private Entrance, Outdoor Area, Free Wi-Fi. Situated in a quiet neighborhood, our apartment is just a short drive from local attractions, Trumbull Mall, parks, restaurants and nearby hiking trails.

4.95 out of 5 average rating, 20 reviews

Home in Shelton

Barn House

Charming, beautiful, spacious farm house originally built in 1773. Meticulously restored and decorated. The perfect getaway for families and friends. Close to downtown Shelton, Bridgeport Ave & Huntington center. This home is breathtaking and on 2 acres of land! Great for exploring, playing, and roasting marshmallows by the fire! The main living room has a wood fire stove which is perfect during the fall and winter. If you’re looking for a relaxing retreat, barn house is for you!

4.93 out of 5 average rating, 55 reviews

Cottage in Seymour

3 Acre Forest, 2 King Beds, Fireplace, BBQ & more

🛏️2 king, 2 twin, BBQ, fireplace, firepit, 1550 sqft entire house 🅿️🛜 Tucked away at the end of a quiet street, set on 3+ acres of lush wooded land, our home is the perfect blend of seclusion and convenience. With a forest as your backyard and RT34 one min away, you can easily balance your desire for nature and adventure with the need for easy travel and commuting, take a short hike into a forest (trails minutes away) and/or relax under the stars around a fire pit.

5 out of 5 average rating, 25 reviews

Apartment in Stratford

Comfortable apartment near all communal facilities

I have an apartment located in an excellent quiet area with easy access. It is furnished and is very close to different areas such as supermarkets, restaurants, hospitals and universities. It also has 100% filtered water to drink. Something very important is that NO type of drugs are accepted, NO Viper or electronic cigarettes or Hookah are NOT accepted on this property. If we find odors or drug residues, they will be reported and fined.

4.99 out of 5 average rating, 96 reviews

Flat in Westville

Retreat in New Haven by Stephanie and Damian

Welcome to your personal retreat in the heart of Westville. This apartment has a spacious spa-like bathroom, and cozy living room with an amazingly comfy couch and large flatscreen tv. You will relax in a cloud of comfort in this centrally located oasis, where you'll find yourself near Yale's football stadium, Westville Bowl music venue, local art studios, quaint coffee shops, and famous restaurants just steps from your door.

4.82 out of 5 average rating, 299 reviews

Guest suite in Shelton

Super cozy 1 BR apt. own entrance, great loc.

Very quiet residential neighborhood, very clean, super cozy apartment with two bedrooms, living room; computer desk with work station, kitchenette (no stove), own bathroom, and amenities. 20 minutes away from Bridgeport, 15 minutes away from Yale, New Haven. Lakes in walking distance, Metro-North rail; 7 minutes, local shopping area 1 mile. Bus route in walking distance. Great neighborhood!! All are welcomed. Warm community.

5 out of 5 average rating, 3 reviews

Flat in New Haven

Tranquil 2BR Retreat Near Yale & Downtown NewHaven

Welcome to your Peaceful retreat in New Haven! This bright and centrally located 2 bedroom apartment is just 10 minutes from downtown and Yale University. Enjoy modern amenities, a cozy and bright ambiance, and easy access to local attractions, making it perfect for leisure and business travelers. Perfect for mindful travelers, work trips, extended stays, or weekend escapes—a home for those who value calm, and good vibes.

4.97 out of 5 average rating, 29 reviews

Flat in East Rock

Cozy East Rock apartment

A spacious and serene space in the heart of East Rock inside a historic home. It is a 5 min drive (or 20 min walk) from Yale's campus and there is a shuttle stop right next to the house on Whitney (blue/orange lines). The private bedroom has a king bed and a shower/bathroom. The sofa in the living room converts to a second bed (queen width) and a second full bathroom (with shower and tub) is located by the kitchen.

Flat in Derby

4.66 out of 5 average rating, 111 reviews

Spacious Renovated 3 bedroom near GriffinHospital

This stylish place to stay is perfect for traveling nurses or group of up to 4 in a lovely, newly renovated, 3 bedroom apartment on the first floor. Temper-Pedic mattresses in two of the bedrooms. Hardwood floor throughout. Open layout in living room and kitchen. Living room has a 75” smart 4K TV. Beautiful bathroom with a standup shower. 5 minute walk to griffin hospital. You will not regret staying here. :)

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Other great holiday rentals in Derby

Private room in Stratford

5 out of 5 average rating, 8 reviews

Quiet, cozy Stratford location

KaitlynRating, 5 stars3 days ago

If you’re staying in or near Stratford, I would suggest staying here! The space is great for two people, and would be comfortable for longer stays. It was also spotlessly clean, smelled phenomenal, and felt super cozy. 10/10, would HIGHLY recommend.

Private room in Stratford

4.94 out of 5 average rating, 32 reviews

Elegant & Cozy Sunlit Room

KathleenRating, 5 stars1 week ago

Great place with good lighting in the bedroom! Host was very kind and proactive.

Private room in Stratford

5 out of 5 average rating, 13 reviews

Cece's Nature Lover Resort

JaeRating, 5 stars1 week ago

Daniela was so kind and accommodating! My stay was only for one night, and Daniela immediately welcomed my booking with her for such a short stay. When I shared I’d hardly eaten during my travel to CT, and after getting stuck at the train station longer than expected, she offered some vegetarian pizza. The room was so cozy between the fan, low lighting, and comfortable bedding. I slept through the night, despite not being the only guest lodging there! It was lovely talking with Daniela and meeting her precious dog. I’m incredibly grateful for the space to rest on the first night of my vacation!

4.93 out of 5 average rating, 85 reviews

Private room in Hamden

Cozy Bedroom in shared Queer home - women only

RebeccaRating, 5 stars6 days ago

Very friendly host! Made us feel comfortable and safe. Clean house and room. There are children in the house, so we heard them playing in the morning, but it was of no issue to us.

Private room in New Haven

4.89 out of 5 average rating, 27 reviews

Aesthetic Room 6 Min From Yale

GeraldineRating, 5 stars1 month ago

Daiana was incredibly helpful and accommodating with all my questions. The apartment is lovely, with a wonderfully powerful shower! The neighbourhood is very residential with no nearby shops or restaurants. But if you are going to an event at the Yale Bowl or nearby sports area (which I was), it is very convenient. And it is less than 10 minutes by car or Uber from downtown New Haven. Daiana's beautiful apartment and very friendly attitude made my stay memorable. Highly recommended!

Private room in New Haven

4.85 out of 5 average rating, 34 reviews

Chapel Room

TeresaRating, 5 stars1 month ago

This was the perfect place for a few day trip to visit New Haven. I was only ever a 10-20 minute walk from the house and it is on a quiet street. There are a couple other rooms occupied but I almost never ran into any one else! If i did people were friendly. The kitchen came in handy and the other amenities were appreciated (wifi, clean bathroom, other furnished and comfy common spaces). I think the most gratitude I felt was at checkout when I was delayed in leaving and I was quickly accommodated. Thanks to Naomi for the lovely stay!

Private room in West Haven

4.94 out of 5 average rating, 86 reviews

Rest, work and recharge by the sea

MariusRating, 5 stars4 days ago

Had a great stay! Super friendly, responsive and helpful hosts. The apartment is a super lovely place with very nice interior. Highly recommend!