Photo by Tim Rousseau

Search Vacation Homes in Darien

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Compare 277 Vacation Homes in Darien with updated reviews, rates, and availability.

Business or Weekend escape

9.6 out of 10, Exceptional, (30)
"Stayed for my other half bday. Place was clean and described well"
The price is AED 294
AED 517 total
includes taxes & fees
1 Jan - 2 January 2025
Business or Weekend escape

Lower Lvl Private 2BR/1BA Family/Pet Friendly

10.0 out of 10, Exceptional, (115)
"Enjoyed the theater room and the comfortable bed"
Lower Lvl Private 2BR/1BA Family/Pet Friendly

Family XMas Bliss: Tree, Cozy Fireplace & Hot Cocoa

10.0 out of 10, Exceptional, (10)
"This home is charming and what a surprise to see a Christmas tree set up! Our family spent Thanksgiving at this perfectly updated home. The home was very clean, functional and the kitchen was well stocked. I would not hesitate to recommend this home."
The price is AED 724
AED 1,802 total
includes taxes & fees
23 Jan - 24 January 2025
Family XMas Bliss: Tree, Cozy Fireplace & Hot Cocoa

Cheerful 4 bedrooms residential house.

9.8 out of 10, Exceptional, (25)
"Great communication and accommodations from the host. We were in town for a concert and the location couldn't have been better! Would recommend this stay for anyone looking within the area."
Cheerful 4 bedrooms residential house.

Welcome to Villa Seabird, Luxury Escape on Long Island Sound

10.0 out of 10, Exceptional, (9)
"This was amazing Thanksgiving with my family. The house is amazing Jon was amazing host and his recommendation for food made you feel like million dollars. Can not thank you enough to share your beautiful home with us and see you in the summer."
Welcome to Villa Seabird, Luxury Escape on Long Island Sound

Remodeled, cozy, family friendly, central place. Entire 2nd & 3rd floor to use.

9.4 out of 10, Exceptional, (8)
"Space was nice. Need top sheets on beds. Noisy location and basement tenant."
The price is AED 1,102
AED 1,623 total
includes taxes & fees
27 Dec - 28 Dec
Remodeled, cozy, family friendly, central place. Entire 2nd & 3rd floor to use.

Adorable Cottage with Water Views, Across the street from Prime & other eateries

9.8 out of 10, Exceptional, (62)
"This home had everything you could ask for. It was very cozy and the owner has put very thoughtful touches into the property. Would definitely stay again!"
Adorable Cottage with Water Views, Across the street from Prime & other eateries

Near NYC ~ Fire pit, Game Room, Pet Friendly, King Bed, Modern Luxury

9.4 out of 10, Exceptional, (8)
"Great place for a group of friends to use as homebase for some shows at the Capitol Theater. "
Near NYC ~ Fire pit, Game Room, Pet Friendly, King Bed, Modern Luxury

Waterview House Walking Distance from Cove Beach

9.0 out of 10, Wonderful, (16)
"The house is beautiful, amazing views! Communication was punctual."
The price is AED 1,921
AED 3,756 total
includes taxes & fees
16 Jan - 17 January 2025
Waterview House Walking Distance from Cove Beach

New Beach Home near Stamford Downtown/Shippan

10.0 out of 10, Exceptional, (16)
"Exactly as advertised, great location, easy check-in, hosts responded immediately to questions. Recommended."
The price is AED 2,039
AED 3,932 total
includes taxes & fees
30 Dec - 31 Dec
New Beach Home near Stamford Downtown/Shippan

Waterfront Retreat Center for Health & Wellness

9.6 out of 10, Exceptional, (54)
"Second time our 24 person family group stayed here, and if anything, it was even better than last year! The location is exceptional, a quiet, private beautiful Victorian era house right on the Sound. The house is roomy, immaculate and very well equipped. Nancy is on top of everything and responds essentially immediately to any and every concern. There aren’t enough superlatives to describe our wonderful experience! "
Waterfront Retreat Center for Health & Wellness

Coastal Retreat: Charming 3-Bedroom Fairfield Townhouse nr Beaches & Town Center

9.8 out of 10, Exceptional, (17)
"This place was super clean and exactly as described. "
Coastal Retreat: Charming 3-Bedroom Fairfield Townhouse nr Beaches & Town Center

PureHeart House, Spacious, Peaceful 3bdr House in Yonkers

9.0 out of 10, Wonderful, (21)
"Long weekend with family to participate in a christening in the Bronx. Place was clean and comfortable. Location was very convenient. Only change I would request would be extra blankets. Otherwise would stay again. "
PureHeart House, Spacious, Peaceful 3bdr House in Yonkers

Captain's Cottage - Cold Spring Harbor Water Views

10.0 out of 10, Exceptional, (53)
"Cute, well-appointed house, great communication, fun stay!"
The price is AED 801
AED 1,616 total
includes taxes & fees
7 Jan - 8 January 2025
Captain's Cottage - Cold Spring Harbor Water Views

Elegant private resort style North Shore home

9.6 out of 10, Exceptional, (17)
"Super easy process. The house is beautiful and very clean. I’m super picky when it comes to cleanliness where I stay. This place is aces. "
Elegant private resort style North Shore home

Charming New York Escape Near Central Park!

7.0 out of 10, Good, (6)
"Got dropped off at the H-Mart from the airport and did my shopping and then walked over, as the host mentioned it was within walking distance and they were right! Super convenient. Well laid out, thoughtful instructions, everything was super easy. Ideal location for a couple of adults to stay to attend a convention. Also, there are workspaces in both of the bedrooms, which was a nice touch. "
Charming New York Escape Near Central Park!

Modern 3 Bdrm Home w/ Parking, Park Views, Backyard, King Bed | Near...

9.2 out of 10, Wonderful, (5)
"It’s nice to have a place for our family of 5 that actually fits us all. Plenty of space and very clean. Thanks "
The price is AED 808
AED 1,792 total
includes taxes & fees
6 Jan - 7 January 2025
Modern 3 Bdrm Home w/ Parking, Park Views, Backyard, King Bed | Near...

Charming duplex with private yard. Close to the beach, dining & shopping!

9.8 out of 10, Exceptional, (36)
"Duplex unit was clean, as described and perfect for our stay visiting family in Rye. Lots of extra towels and nice welcoming snacks in the kitchen. Super convenient location. Will likely stay there again. "
Charming duplex with private yard. Close to the beach, dining & shopping!

Historic Hideaway with Lake Access!

9.6 out of 10, Exceptional, (12)
"Overall, very nice historic home. Very clean, perfect location for our family holiday, wonderful mattresses on all beds, well stocked kitchen with all cooking necessities. Good communication with owners who promptly helped to rectify a few issues. Would recommend to anyone looking to stay in this area."
Historic Hideaway with Lake Access!

ZEN HOUSE Historic Sculptor Studio creator or Mount Rushmore midcentury home

10.0 out of 10, Exceptional, (24)
"Pre-stay communication was excellent, with our host contacting me with suggestions for outings (I asked). Our host met us, gave us a tour of the property - not just the living space but the grounds, too. The house is cozy, well thought out and has small touches like a deck of cards (in case you have a couple of minutes of downtime), a beautiful tea set with a variety of delicious teas to use. The house is thoughtfully decorated, the couch and bed are comfortable and there is plenty of space for...
ZEN HOUSE Historic Sculptor Studio creator or Mount Rushmore midcentury home
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.
Don't see what you're looking for?
See all available properties in Darien
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Darien

Stamford Suites

2.5 star property
6.8 out of 10, (772)
"It was in walking distance of the event we were going to."
The price is AED 515
AED 592 total
includes taxes & fees
1 Jan - 2 January 2025
Stamford Suites

DUNE Fairfield Beach

3.0 star property
8.8 out of 10, Excellent, (45)
"The property is generally old, but it was a nice renovation. Of the room. "
The price is AED 734
AED 1,215 total
includes taxes & fees
27 Dec - 28 Dec
DUNE Fairfield Beach

Business or Weekend escape

9.6 out of 10, Exceptional, (30)
"Stayed for my other half bday. Place was clean and described well"
The price is AED 294
AED 517 total
includes taxes & fees
1 Jan - 2 January 2025
Business or Weekend escape
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.