Darien Vacation Rentals

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Our top choices for Darien vacation rentals

Stylish Sheek Loft Dwntwn, Amphitheater, Park, Metro North, Ferry All 2-10min

Stylish Sheek Loft Dwntwn, Amphitheater, Park, Metro North, Ferry All 2-10min
Downtown Bridgeport
9.0 out of 10, Wonderful, (6 reviews)
"Nice little spot with a great host."
United States
J M.
$158 nightly
The price is $179
May 12 - May 13
Total with taxes and fees
Stylish Sheek Loft Dwntwn, Amphitheater, Park, Metro North, Ferry All 2-10min

Business or Weekend escape

Business or Weekend escape
Stratford
9.2 out of 10, Wonderful, (54 reviews)
"Clean room, easy check-in, parking available on-site "
United States
Cindy
$130 nightly
The price is $147
May 10 - May 11
Total with taxes and fees
Business or Weekend escape

Renovated 2BR Retreat / Modern Comforts Included

Renovated 2BR Retreat / Modern Comforts Included
West End - West Side
10.0 out of 10, Exceptional, (2 reviews)
"Very pretty, clean place for us to stay while visiting family. Communication was very timely. Would definitely stay here again"
United States
Deborah
$255 nightly
The price is $289
May 7 - May 8
Total with taxes and fees
Renovated 2BR Retreat / Modern Comforts Included

Charming 1-bedroom artist den with WiFi, AC in terrific Huntington

Charming 1-bedroom artist den with WiFi, AC in terrific Huntington
Huntington
9.8 out of 10, Exceptional, (7 reviews)
"Host was very accommodating - lovely property!"
United States
Mary C.
$199 nightly
The price is $227
May 13 - May 14
Total with taxes and fees
Charming 1-bedroom artist den with WiFi, AC in terrific Huntington

Cozy Studio/apartment

Cozy Studio/apartment
Stratford
10.0 out of 10, Exceptional, (1 review)
"Nice little apartment for a short stay. There was some issues with a leaky faucet, however the host was very responsive and accommodating to getting it fixed."
United States
Katerina c.
$196 nightly
The price is $222
May 7 - May 8
Total with taxes and fees
Cozy Studio/apartment

Luxury Designer 2 bedroom+office/3bed vacation home.

Luxury Designer 2 bedroom+office/3bed vacation home.
Brooklawn - St. Vincent
9.4 out of 10, Exceptional, (22 reviews)
"We stayed here for three nights, and it was very comfortable, clean and spacious. It's in a good location and the walk up to the second floor was not too bad. It was as advertised, and we would stay there again when in Bridgeport. "
United States
Robert C.
$335 nightly
The price is $380
May 7 - May 8
Total with taxes and fees
Luxury Designer 2 bedroom+office/3bed vacation home.

DUNE Fairfield Beach

DUNE Fairfield Beach
3.0 star property
Fairfield Beach
9.0 out of 10, Wonderful, (85 reviews)
"The room was spotless and cozy and the location couldn't be better! "
United States
Samantha
$252 nightly
The price is $290
May 12 - May 13
Total with taxes and fees
DUNE Fairfield Beach

Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi

Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
Waterside
10.0 out of 10, Exceptional, (12 reviews)
"Fantastic place. We had a great stay!"
United States
Sara C.
$304 nightly
The price is $345
May 10 - May 11
Total with taxes and fees
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi

Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC

Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC
Kings Park
10.0 out of 10, Exceptional, (19 reviews)
"Wonderful all-around, clean, definitely a great experience for my first VRBO stay. "
United States
Tyler M.
$161 nightly
The price is $184
May 10 - May 11
Total with taxes and fees
Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC

The Blue Sapphire: Modern & Stylish 2BR w/ 2 King Beds & Full Kitchen

The Blue Sapphire: Modern & Stylish 2BR w/ 2 King Beds & Full Kitchen
Brooklawn - St. Vincent
8.0 out of 10, Very Good, (1 review)
"It was clean "
United States
Burton
$255 nightly
The price is $289
May 7 - May 8
Total with taxes and fees
The Blue Sapphire: Modern & Stylish 2BR w/ 2 King Beds & Full Kitchen

Zen, Spacious & Comfy 2 bed, Lux beds

Zen, Spacious & Comfy 2 bed, Lux beds
Brooklawn - St. Vincent
$286 nightly
The price is $324
May 7 - May 8
Total with taxes and fees
Zen, Spacious & Comfy 2 bed, Lux beds

Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!

Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!
Downtown Stamford
9.2 out of 10, Wonderful, (11 reviews)
"Perfect apartment and location. Amazing communication. Thank you!!"
United States
Ryan F.
$275 nightly
The price is $312
May 11 - May 12
Total with taxes and fees
Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!

2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
Greenwich
9.8 out of 10, Exceptional, (33 reviews)
"Beautiful space, excellent communication from the hosts. Would stay again!"
United States
Crystal
$283 nightly
The price is $321
May 20 - May 21
Total with taxes and fees
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

Centric property close to all the great things in the city

Centric property close to all the great things in the city
Brooklawn - St. Vincent
7.0 out of 10, Good, (14 reviews)
"Having a microwave would also help with the amenities. Overall good. "
United States
Karen A.
$233 nightly
The price is $264
May 10 - May 11
Total with taxes and fees
Centric property close to all the great things in the city

Renovated Cape Near beach, with Fire Pit and BBQ, 1 mile to NYC train

Renovated Cape Near beach, with Fire Pit and BBQ, 1 mile to NYC train
Fairfield
10.0 out of 10, Exceptional, (11 reviews)
"Great clean, kid-friendly house in just the location we wanted. Lots of thoughtful touches throughout the house that made our stay very comfortable. Would stay again!"
United States
Mary G.
$457 nightly
The price is $517
May 11 - May 12
Total with taxes and fees
Renovated Cape Near beach, with Fire Pit and BBQ, 1 mile to NYC train

Modern 2 Bed in BlackRock

Modern 2 Bed in BlackRock
Black Rock Historic District
6.8 out of 10, (3 reviews)
"Cozy get away"
United States
Anonymous traveler
$296 nightly
The price is $335
May 11 - May 12
Total with taxes and fees
Modern 2 Bed in BlackRock

Luxe Provincial Style Studio w/ Patio & Parking

Luxe Provincial Style Studio w/ Patio & Parking
Huntington Station
10.0 out of 10, Exceptional, (3 reviews)
"This stay was perfect for what I needed. The studio was clean, roomy, and had A A/C, which was needed on the muggy hot days there. If I'm in the area again, this will be my spot. "
United States
Elizabeth
$337 nightly
The price is $385
May 7 - May 8
Total with taxes and fees
Luxe Provincial Style Studio w/ Patio & Parking

Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!

Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!
Port Chester
10.0 out of 10, Exceptional, (31 reviews)
"Super cute with everything we needed! We had a great time during our stay and this was the perfect spot for a little getaway! Highly recommend!"
United States
Christina
$361 nightly
The price is $413
May 11 - May 12
Total with taxes and fees
Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!

Captain's Cottage - Cold Spring Harbor Water Views

Captain's Cottage - Cold Spring Harbor Water Views
Cold Spring Harbor
10.0 out of 10, Exceptional, (76 reviews)
"Location was perfect!"
United States
Linda J P.
$465 nightly
The price is $531
May 11 - May 12
Total with taxes and fees
Captain's Cottage - Cold Spring Harbor Water Views

Spacious Studio with Pool Table

Spacious Studio with Pool Table
Westport
8.6 out of 10, Excellent, (7 reviews)
"The room was great, the location was good and there was a pool table! "
United States
Eadweard
$253 nightly
The price is $275
May 11 - May 12
Total with taxes and fees
Spacious Studio with Pool Table
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 Darien Hotel Reviews

Find out more about Darien

Everything you need to know about Darien vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Darien vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Darien vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Darien vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Darien. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Darien in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $145 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Darien rentals

At Expedia, we put the best Darien vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Darien rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Darien vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Darien. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Can I find a vacation rental in Darien?

Yes, we give you a choice of vacation rentals close to top sights in Darien, or you can choose a secluded option if you'd like a relaxing place to stay. Darien is known for its parks and shopping. Make sure you have time to check out the beaches and restaurants during your trip.

What are some of the best vacation rentals that Darien has to offer?

Modern 5BR Home W/Private Backyard Basket Ball Hoop Near NY& Long Island Beaches: Visitors like this Darien vacation home rental. It offers a garden, a barbecue grill, and air-conditioning to help you feel perfectly comfortable in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

How many vacation rentals are there in Darien?

With 13 Expedia vacation rentals, you're sure to find just the right place for your Darien stay.

What can I see and do in Darien?

Cove Island Park and Woodway Park are a couple of lovely local spots to get outside and enjoy nature. Other places in town to visit include The Mather Homestead and Valley Street Open Space.

What are vacation rentals like in Darien?

Vacation rentals are private accommodations you can reserve for several days or longer in Darien. Vacation rentals provide amenities such as patios, hot tubs, and fire pits so you'll feel just like you're staying in your own home. If you're concerned about cleanliness, a vacation rental can provide a sense of safety away from public hotel elevators and bustling concierge desks while still allowing you the enjoyment of travel. You'll also find more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is an attractive choice for family trips or small group gatherings.