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Check prices for these dates

Next weekend
23 May - 25 May
In two weeks
30 May - 1 Jun
In one month
13 Jun - 15 Jun
In two months
11 Jul - 13 Jul

Compare 361 Vacation Homes in Darien with updated reviews, rates, and availability.

Historic Connecticut Home w/ Grill & Spacious Yard
Dining

Historic Connecticut Home w/ Grill & Spacious Yard

10.0 out of 10, Exceptional, (9)
"Very well appointed (Boll & Branch sheets so nice). Great communication from owners. "
Historic Connecticut Home w/ Grill & Spacious Yard
Captain's Cottage - Cold Spring Harbor Water Views
Aerial view

Captain's Cottage - Cold Spring Harbor Water Views

10.0 out of 10, Exceptional, (60)
"Everything was awesome! Would definitely stay here again! "
The price is AED 790
AED 1,800 total
includes taxes & fees
20 May - 21 May
Captain's Cottage - Cold Spring Harbor Water Views
Lakeside luxury: beautiful, relaxing 4 bedroom home
Property grounds

Lakeside luxury: beautiful, relaxing 4 bedroom home

10.0 out of 10, Exceptional, (20)
"This property was perfect for our weekend trip to celebrate my nieces family/birthday weekend at Fairfield"
Lakeside luxury: beautiful, relaxing 4 bedroom home
Business or Weekend escape
Pool

Business or Weekend escape

9.6 out of 10, Exceptional, (36)
"Very nice owner with great communication. "
The price is AED 275
AED 496 total
includes taxes & fees
14 May - 15 May
Business or Weekend escape
PureHeart House, Spacious, Peaceful 3bdr House in Yonkers
Fridge, microwave, oven, stovetop

PureHeart House, Spacious, Peaceful 3bdr House in Yonkers

8.8 out of 10, Excellent, (30)
"Its was perfect, quiet and spacious great little get away."
PureHeart House, Spacious, Peaceful 3bdr House in Yonkers
Cheerful 4 bedrooms residential house.
Fridge, microwave, dishwasher, coffee/tea maker

Cheerful 4 bedrooms residential house.

9.8 out of 10, Exceptional, (30)
"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.
Luxury 3Bed Private Apartment Near Manhattan
Smart TV, computer monitors, printers

Luxury 3Bed Private Apartment Near Manhattan

9.2 out of 10, Wonderful, (14)
"Host was very accommodating and easy to communicate with!"
The price is AED 1,194
AED 2,218 total
includes taxes & fees
18 May - 19 May
Luxury 3Bed Private Apartment Near Manhattan
Bright Stylish Chic 4BR 4BA Home Pet Friendly!
Fridge, microwave, oven, stovetop

Bright Stylish Chic 4BR 4BA Home Pet Friendly!

10.0 out of 10, Exceptional, (96)
"Very convenient and plenty of room. Easy to get to NY from Stamford train station and everything we needed nearby."
Bright Stylish Chic 4BR 4BA Home Pet Friendly!
Main Street Westport, walk to shops, dining, downtown
Miscellaneous

Main Street Westport, walk to shops, dining, downtown

Main Street Westport, walk to shops, dining, downtown
Over Sized Colonial on Private Road.
Exterior

Over Sized Colonial on Private Road.

9.6 out of 10, Exceptional, (39)
"We were a family of 4 adults and 2 toddlers staying over Thanksgiving. We really didn’t need all the space but we certainly enjoyed it. There’s a huge well stocked kitchen, kids’ play areas on both the main floor and basement, and the property is massive and gorgeous. Great stay!"
Over Sized Colonial on Private Road.
New Beach Home near Stamford Downtown/Shippan
Terrace/patio

New Beach Home near Stamford Downtown/Shippan

10.0 out of 10, Exceptional, (20)
"We had a great time and it was a very spacious and clean location "
The price is AED 2,130
AED 3,918 total
includes taxes & fees
20 May - 21 May
New Beach Home near Stamford Downtown/Shippan
Glen Cove Home: Walk to Boardwalk + Dining!
Fridge, microwave, stovetop, dishwasher

Glen Cove Home: Walk to Boardwalk + Dining!

9.2 out of 10, Wonderful, (15)
"We enjoyed staying here for a long weekend while touring maritime colleges in the area. This nice quiet neighborhood was restful at the end of each day and convenient to everywhere we needed to be. The nearby brewery on the harbor was a great spot for lunch."
Glen Cove Home: Walk to Boardwalk + Dining!
Westport Gem - walk to shops, dining, town center, pet-friendly
Miscellaneous

Westport Gem - walk to shops, dining, town center, pet-friendly

10.0 out of 10, Exceptional, (3)
"Had a great time! My favorite part was sitting on the back deck w coffee in the morning. There were so many birds and the tall hedges that protected the privacy was so charming. The host was so nice and left out fruit and snacks. Loved staying there!"
Westport Gem - walk to shops, dining, town center, pet-friendly
Spacious Gorgeous Getaway perfect for family reunion or business
Fridge, microwave, oven, stovetop

Spacious Gorgeous Getaway perfect for family reunion or business

9.8 out of 10, Exceptional, (6)
"House was perfect for the group. We had everything we needed and plenty of room for us. Owner was great with communications before and during our stay"
Spacious Gorgeous Getaway perfect for family reunion or business
Cozy and beautiful house
Interior

Cozy and beautiful house

9.8 out of 10, Exceptional, (24)
"Property owner was great at communicating and the house was perfect!"
Cozy and beautiful house
Charming Mamaroneck Home ~ 22 Mi to Manhattan
TV

Charming Mamaroneck Home ~ 22 Mi to Manhattan

7.8 out of 10, Good, (12)
"Clean and easy check in--Great Location!"
Charming Mamaroneck Home ~ 22 Mi to Manhattan
Ossining Vacation Rental Near River, Trails & MTA!
Fridge, microwave, stovetop, dishwasher

Ossining Vacation Rental Near River, Trails & MTA!

7.6 out of 10, Good, (8)
"This was our Christmas gathering place for family from 4 states. Beautiful home and location. "
Ossining Vacation Rental Near River, Trails & MTA!
Breathtaking Waterfront house
Outdoor pool

Breathtaking Waterfront house

9.4 out of 10, Exceptional, (3)
"Fun property, kitchen needs a little organizing, And instructions for tv and remotes would be helpful"
Breathtaking Waterfront house
Cozy retreat with fenced in yard—centrally located in the heart of Long Island.
Sun loungers, beach towels

Cozy retreat with fenced in yard—centrally located in the heart of Long Island.

10.0 out of 10, Exceptional, (12)
"Clean, cozy and would stay again."
Cozy retreat with fenced in yard—centrally located in the heart of Long Island.
Waterfront Retreat Center for Health & Wellness
Property grounds

Waterfront Retreat Center for Health & Wellness

9.6 out of 10, Exceptional, (56)
"Very comfortable stay with lots of room to spread out. Interesting older house with many unique features. We were happy to learn that they recently installed a new furnace and a dishwasher. Lots of cookware and dishes. We spread out over two dining rooms for mealtime which worked well for us. "
Waterfront Retreat Center for Health & Wellness
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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Other property types in Darien

Night Hotel Broadway
Reception

Night Hotel Broadway

2.5 star property
6.8 out of 10, (2020)
"Fantastic location, great accommodations, and excellent staff."
The price is AED 408
AED 536 total
includes taxes & fees
26 May - 27 May
Night Hotel Broadway
LIC Manhattan View Hotel
Front of property

LIC Manhattan View Hotel

2.0 star property
8.8 out of 10, Excellent, (82)
"Amazing stay "
The price is AED 551
AED 645 total
includes taxes & fees
28 May - 29 May
LIC Manhattan View Hotel
Hyatt Place Fort Lee / George Washington Bridge
Desk, blackout drapes, soundproofing, iron/ironing board

Hyatt Place Fort Lee / George Washington Bridge

3.0 star property
8.8 out of 10, Excellent, (1604)
"Excelente Hotel "
The price is AED 624
AED 716 total
includes taxes & fees
26 May - 27 May
Hyatt Place Fort Lee / George Washington Bridge
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.