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Vacation rentals in Derby

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Top-rated vacation rentals in Derby

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Rental unit in Milford

4.94 out of 5 average rating, 136 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!

Home in East Haven

4.96 out of 5 average rating, 131 reviews

The Breakaway - a waterfront gem.

Located next to historic Lighthouse Park, this Morgan Point, California-style bungalow overlooks a lighthouse and breakwater that protect New Haven Harbor. Prepare oceanfront dinners in your modern kitchen; relax to sunrises, sunsets, & the sound of waves. A quiet beach is steps from the door for swimming and kayaking. New Haven sights, restaurants, & nightlife are only minutes away. Picturesque coastline communities, local vineyards, breweries, fall foliage, & commuter rail to NYC are nearby.

Guesthouse in Southbury

4.93 out of 5 average rating, 307 reviews

Charming Guest Cottage with Modern Amenities

Private Guest House set on 5+ Acres, along with Historic Colonial Home. Bright and sunny and over looks pool and gardens (seasonal). Efficiency with Kitchen featuring 2 burner stove, Microwave, Under Counter Fridge/Freezer/Ice Maker, Dishwasher, Granite Counters. . Dining Area, Great Room w/ soaring ceilings, French Doors to private patio, hardwood floors. Loft with full-sized bed, and sofa can be a to Queen Size Sleeper. Full bath with extra-large shower. Dog friendly (approval needed).

Guest suite in Fairfield

4.94 out of 5 average rating, 139 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.

Rental unit in Woodmont

4.97 out of 5 average rating, 550 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!

Rental unit in New Haven

4.99 out of 5 average rating, 174 reviews

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.

Home in Monroe

4.96 out of 5 average rating, 199 reviews

Garden Level Suite with Beautiful Pool

Enjoy complete privacy and 900+ square feet of living space in the ground floor suite/apartment of our home. Complete with its own private entrance and personal garage - our ground floor suite is your own private domain. There is one king bed, one queen bed, and a comfy sectional couch. Enjoy a small kitchenette for simple cooking inside, and an alfresco BBQ for bigger cooking. There is plenty of living space inside and out! A new washer/dryer unit will take care of all the pool towels used!

Bungalow in Woodmont

4.98 out of 5 average rating, 267 reviews

Fall Sale!Beach Bungalow|Walk to Beach|Petfriendly

Welcome to the Beach Bungalow, completely remodeled to the studs in '21! This Woodmont by the Sea home is a 3 block stroll to Anchor Beach & the walkway along beautiful Beach Ave. The home offers a modern kitchen, dining for 6, private back porch & outdoor shower. This +775sf bungalow has a driveway & on-street pkg. It's located in a charming coastal town, walking distance to restaurants, grocery store & Robert Treat Farm and is 2 mi to I95, 10 mi to Yale/New Haven...and mins to breweries.

Loft in Woodmont

4.93 out of 5 average rating, 126 reviews

Lovely water front lower-level loft, free parking

This unique centrally located water front loft is located on the second Gulf Pond 1.5 miles from historic Milford center buzzing with water front restaurants and downtown shopping. This one bedroom, one bath, has a private entrance and free off street parking. Outdoor patio & grill with kitchenette, enjoy a waterfront view throughout the 400 sq ft space. Close to I-95, the Merrit Parkway, and Milford train station. Explore 17 miles of beaches in this New England town by bike, kayak, or foot.

Guesthouse in Westville

4.94 out of 5 average rating, 281 reviews

Square 6ix

Inviting, eclectic, and completely private, this single family stand-alone guest house is an intimate and engaging haven. Stylishly decorated with mid-century modern furniture and adorned with pieces from local artists, this quiet home has a separate entrance, separate porch, high ceilings, and a fully equipped kitchen. The guest house is located a walking-block away from the charms of Westville Village and Edgewood Park.

Guest suite in Woodbridge

4.92 out of 5 average rating, 143 reviews

Cupola Hill -a 2 BR guest suite with bucolic views

Beautiful 2 bedroom guest suite attached to main house with separate entrance, bathroom, living room. Set on magnificent 20 acre estate, perfect country get away, only 15 minutes to Yale and downtown New Haven. It’s the best of both worlds! Come enjoy the great restaurants of New Haven and then head to Cupola Hill for an evening in the country! Have a glass of wine under the stars and watch the wildlife!

Guest suite in Wallingford

5 out of 5 average rating, 541 reviews

Wintergreen Gardens Suite @ William Becroft House

LGBTQ friendly. Our 1915 Arts & Crafts bungalow's spacious in-law suite offers driveway parking, private entrance, sunroom, king bedroom, en-suite bath, kitchenette w/fridge, micro, coffee maker, toaster. Relax in bed with 40" HDTV with Amazon Prime, HBO Max, Netflix, premium cable. Enjoy private gardens to sun, read a book or cup of coffee. Short drive to 4 Vineyards, Theater and the train station.

Vacation rentals for every style

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Popular amenities for Derby vacation rentals

Free parking on premises

Air conditioning

Stay near Derby's top sights

Indian Well State Park19 locals recommend

Target17 locals recommend

Griffin Hospital9 locals recommend

BAD SONS Beer Company9 locals recommend

Big Y World Class Market9 locals recommend

River Rock Tavern7 locals recommend

Other great vacation rentals in Derby

Cabin in Trumbull

4.93 out of 5 average rating, 70 reviews

Rustic cabin with spectacular lake view

Guesthouse in Milford

5 out of 5 average rating, 52 reviews

The studio downtown

Rental unit in Bridgeport

5 out of 5 average rating, 38 reviews

Beautiful, clean and quiet place to relax

Cottage in Branford

4.97 out of 5 average rating, 75 reviews

Enchanted Cottage on the Marsh, walk to beach

Rental unit in Bridgeport

5 out of 5 average rating, 31 reviews

Ricport Studio 2

Guest suite in West Haven

4.87 out of 5 average rating, 63 reviews

Midcentury Lakeside Guest Suite

Rental unit in Westville

4.99 out of 5 average rating, 77 reviews

Retreat in New Haven by Stephanie and Damian

Rental unit in Shelton

4.9 out of 5 average rating, 10 reviews

Cozy Beautiful 2BR 1BA Hideaway Minutes 2 Yale

Quick stats about vacation rentals in Derby

Total rentals
30 properties
Nightly prices starting at
$40 before taxes and fees
Total number of reviews
1.8K reviews
Family-friendly rentals
10 properties are a good fit for families
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
30 properties include access to wifi

Frequently Asked Questions

Do apartment rentals in Derby have a kitchen?
Absolutely! We offer over 10 apartment rentals with a kitchen in Derby. Enjoy a tailored experience with all the comforts you desire.
Are there vacation rentals with a dedicated workspace in Derby?
Yes! Work meets play with ease at over 10 vacation rentals in Derby featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do apartment rentals in Derby have air conditioning?
Absolutely! We offer over 10 apartment rentals with air conditioning in Derby. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for House Rentals in Derby?
Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with wifi, over 10 homes with air conditioning, over 10 homes with a kitchen, over 10 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.
Do apartment rentals in Derby have free parking?
Absolutely! We offer over 10 apartment rentals with free parking in Derby. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly vacation rentals in Derby?
Derby has more than 10 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Do apartment rentals in Derby have wifi?
Absolutely! We offer over 10 apartment rentals with wifi in Derby. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in apartment rentals in Derby?
Experience the best of Derby with our apartment rentals, starting at about $80 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

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