Derby Vacation Rentals

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Check prices for these dates

In two weeks
Dec 26 - Dec 28
In two months
Feb 6 - Feb 8
In three months
Mar 6 - Mar 8
In four months
Apr 3 - Apr 5

Our top choices for Derby vacation rentals

Private beach nearby, sun loungers, beach umbrellas, beach towels
DUNE Fairfield Beach

Apartment in Fairfield

DUNE Fairfield Beach
3.0 star property
9.0 out of 10, Wonderful, (77)
"The room was spotless and cozy and the location couldn't be better! "
United States
Samantha
DUNE Fairfield Beach
Honeymoon Apartment, 3 Bedrooms, Kitchen | In-room dining
Luxury Furnished Apartments by Hyatus Downtown at Yale

Aparthotel in The Hill

Luxury Furnished Apartments by Hyatus Downtown at Yale
3.5 star property
9.6 out of 10, Exceptional, (61)
"Loved our stay here. "
United States
Christina
Luxury Furnished Apartments by Hyatus Downtown at Yale
Terrace/patio
Lakeside/Sleeps20/HotTub/GameRoom/2Acres/Firepit

Vacation Home in Brookfield

Lakeside/Sleeps20/HotTub/GameRoom/2Acres/Firepit
9.6 out of 10, Exceptional, (4)
"The host was very kind and welcoming. The home was spacious and the perfect setting for our celebration weekend. Everyone had their own space and we had multiple spaces for group activities. We enjoyed our time and appreciate the hospitality. "
United States
Valerie V.
Lakeside/Sleeps20/HotTub/GameRoom/2Acres/Firepit
Dining
Peaceful Vintage Home with Private Pond in Redding, CT.

Vacation Home in Redding

Peaceful Vintage Home with Private Pond in Redding, CT.
2.0 star property
9.4 out of 10, Exceptional, (3)
"Several of us stayed for one night for our kids soccer tournament. The home was spacious and had all the amenities needed to make our short stay comfortable. The host was very responsive and accommodating. "
United States
Annette H.
The price is ￥63,512
￥101,266 total
includes taxes & fees
Dec 15 - Dec 16
Peaceful Vintage Home with Private Pond in Redding, CT.
Pool
Business or Weekend escape

Vacation Home in Stratford

Business or Weekend escape
9.2 out of 10, Wonderful, (51)
"Clean room, easy check-in, parking available on-site "
United States
Cindy
The price is ￥13,238
￥22,816 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Business or Weekend escape
4 bedrooms, iron/ironing board, free WiFi, bed sheets
Waterfront Cottage in Branford

Cottage in branford

Waterfront Cottage in Branford
10.0 out of 10, Exceptional, (98)
"Beautiful location "
United States
Anne d.
Waterfront Cottage in Branford
Fridge, microwave, oven, stovetop
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.

Apartment in Cheshire

Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
9.4 out of 10, Exceptional, (13)
"Needed a place to sleep for a couple of nights and this worked for us."
United States
James (Jim) L.
The price is ￥19,483
￥33,308 total
includes taxes & fees
Dec 24 - Dec 25
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
1 bedroom, desk, iron/ironing board, WiFi
One bedroom apartment in United States of America, New Haven

Apartment in Dwight

One bedroom apartment in United States of America, New Haven
10.0 out of 10, Exceptional, (2)
"Apartment was very clean and well supplied, host very responsive. Location is convenient to Yale and restaurants. As noted in the listing, you'll have to carry your luggage up 4 flights of stairs. There is some street noise as is typical for that part of the city. Very happy with it overall and plan to stay again."
United States
Philip S.
The price is ￥14,795
￥31,926 total
includes taxes & fees
Jan 9 - Jan 10, 2026
One bedroom apartment in United States of America, New Haven
Seasonal outdoor pool
Luxury Apartments by Hyatus at Pierpont

Aparthotel in The Hill

Luxury Apartments by Hyatus at Pierpont
4.0 star property
9.4 out of 10, Exceptional, (22)
"Easily accessible, very clean and pleasant place to stay."
Canada
Kirsten
Luxury Apartments by Hyatus at Pierpont
Beach nearby, beach towels
Gorgeous 4BR Beach House with Private Beach Access.

Vacation Home in Pine Orchard

Gorgeous 4BR Beach House with Private Beach Access.
9.8 out of 10, Exceptional, (76)
"Nice property, thanks to the owners.Jackie"
United States
Jacqueline M.
Gorgeous 4BR Beach House with Private Beach Access.
Interior
Stunning Apt W/ Parking and Gym | Downtown at Yale

Apartment in The Hill

Stunning Apt W/ Parking and Gym | Downtown at Yale
10.0 out of 10, Exceptional, (46)
"High quality experience, walking distance to all we needed, clean and spacious. Excellent support and communication from the hosts, would stay again."
United Kingdom
Coco N.
Stunning Apt W/ Parking and Gym | Downtown at Yale
1 bedroom, iron/ironing board, WiFi, bed sheets
Downtown New Haven Escape

Apartment in Dwight

Downtown New Haven Escape
2.0 star property
8.0 out of 10, Very Good, (6)
"Great place to stay, a little tight for 2 people but good for a single. Well appointed and a great location in the city. Would definitely recommend a stay here."
United States
Michael H.
The price is ￥21,414
￥39,282 total
includes taxes & fees
Dec 24 - Dec 25
Downtown New Haven Escape
Property grounds
Candlewood Lake - Family Getaway with direct lake access. 3775 sqft home.

Vacation Home in Danbury

Candlewood Lake - Family Getaway with direct lake access. 3775 sqft home.
10.0 out of 10, Exceptional, (24)
"Beautiful property with amazing lake views and water access."
United States
Sophia C.
Candlewood Lake - Family Getaway with direct lake access. 3775 sqft home.
Exterior
New One Bedroom Apartment Centrally Located in Southbury

Apartment in Southbury

New One Bedroom Apartment Centrally Located in Southbury
9.8 out of 10, Exceptional, (19)
"Perfect sized apartment for a short stay - very convenient to my destination"
United States
S
The price is ￥14,017
￥19,234 total
includes taxes & fees
Dec 24 - Dec 25
New One Bedroom Apartment Centrally Located in Southbury
Dining
Coastal Holiday Retreat: Luxury Waterfront, Hot Tub & Private Beach

Vacation Home in Branford

Coastal Holiday Retreat: Luxury Waterfront, Hot Tub & Private Beach
10.0 out of 10, Exceptional, (71)
"We had a wonderful vacation!! The house was perfect, check in couldn’t have easier and the views couldn’t have been better. A perfect summer getaway."
United States
Mike S.
Coastal Holiday Retreat: Luxury Waterfront, Hot Tub & Private Beach
Exterior
Charming Colonial for Events! – Perfect for Family Reunions and Group Getaways!

Vacation Home in North End

Charming Colonial for Events! – Perfect for Family Reunions and Group Getaways!
9.4 out of 10, Exceptional, (6)
"This property is absolutely beautiful. Extremely clean. The host was very attentive to my questions before and after check in. The host checked on my family during our stay. The yard, the porches, and the entire interior are so cozy and comfortable. The check in and check out processes were smooth. The neighborhood is quiet. I am already looking forward to going back! Definitely recommend the Beechmont House"
United States
April R.
The price is ￥136,662
￥247,102 total
includes taxes & fees
Dec 19 - Dec 20
Charming Colonial for Events! – Perfect for Family Reunions and Group Getaways!
1 bedroom, WiFi, bed sheets
Private Third-Floor Attic Apartment Full Kitchen • King Bed • Backyard Access

Apartment in West New Haven

Private Third-Floor Attic Apartment Full Kitchen • King Bed • Backyard Access
2.0 star property
9.4 out of 10, Exceptional, (3)
"Great communication and easy check in, would recommend "
United States
Ethan R.
The price is ￥12,546
￥20,269 total
includes taxes & fees
Dec 16 - Dec 17
Private Third-Floor Attic Apartment Full Kitchen • King Bed • Backyard Access
Fridge, microwave, oven, stovetop
Modern Apartment in Black Rock

Apartment in Black Rock Historic District

Modern Apartment in Black Rock
2.0 star property
9.6 out of 10, Exceptional, (12)
"Visited with family for the weekend and the property manager was great with communication and the location was fantastic."
United States
Caroline C.
Modern Apartment in Black Rock
Shared Dormitory, 1 Bedroom | Outdoor dining
Room-plaid Room 3min From Yale Univ

Vacation Home in Newhallville

Room-plaid Room 3min From Yale Univ
3.0 star property
10.0 out of 10, Exceptional, (1)
"The owner is great and made great accommodations for our stay, the price was wonderful. The neighborhood maybe wasent the nicest but thats kinda out of his control."
United States
Colby
Room-plaid Room 3min From Yale Univ
On the beach, sun loungers, beach towels
Beach Front Arts & Crafts House With Gorgeous Views Of The Sound

Vacation Home in Milford

Beach Front Arts & Crafts House With Gorgeous Views Of The Sound
10.0 out of 10, Exceptional, (134)
"Wonderful stay in a nice quiet neighborhood "
United States
Jacob M.
Beach Front Arts & Crafts House With Gorgeous Views Of The Sound
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Derby Hotel Reviews

Wyndham Southbury

Wyndham Southbury

10/10 Excellent
"Little dated but very nice for the price."
Anthony 1-night trip
Posted 1 day ago
Wyndham Southbury

Find out more about Derby

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Frequently asked questions

Are there vacation rentals in Derby?

Yes, we offer vacation rentals near top attractions in Derby, or you can go with a secluded option if you'd like a relaxing place to stay. Derby is known for its parks and museums.

What are some of the best vacation rentals in Derby?

Lakeside/Sleeps20/HotTub/GameRoom/2Acres/Firepit: Visitors like this Derby vacation home rental. It is located on a lake and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 6 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, an arcade game room, and a hot tub so you can immerse yourself in your vacation.

What’s there to see and do in Derby?

While exploring the area, visit family-friendly sights like SportsCenter of Connecticut, or get outside and enjoy nature at Housatonic River. While here, Osborne Homestead Museum and Osborndale State Park are other places worth a visit.

What’s a vacation rental in Derby like?

A vacation rental is a private property you can stay in for several days or longer in Derby. Vacation rentals provide amenities like WiFi and washers and dryers so your stay will be comfortable. If you're concerned about a sanitized environment, a vacation rental can offer a sense of safety away from shared hotel elevators and busy lobbies while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a traditional hotel, which makes a vacation rental an attractive choice for small groups.