Search Vacation Homes in Annandale-on-Hudson

  • 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
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

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 701 Vacation Homes in Annandale-on-Hudson with updated reviews, rates, and availability.

Esopus Creek modern Tiny house Retreat!
Outdoor dining

Esopus Creek modern Tiny house Retreat!

9.6 out of 10, Exceptional, (30)
"Had a fantastic stay for a quick overnight trip to ski."
The price is AEDĀ 569
AEDĀ 897 total
includes taxes & fees
14 May - 15 May
Esopus Creek modern Tiny house Retreat!
HOT TUB w/ POOL, STREAM on 7 Acres, JUST 2 MINUTES FROM TOWN
Terrace/patio

HOT TUB w/ POOL, STREAM on 7 Acres, JUST 2 MINUTES FROM TOWN

10.0 out of 10, Exceptional, (95)
"This Woodstock gem is a lovely and spacious getaway spot. We had plenty of room for two couples and our dogs to stay comfortably for multiple days. The house is very close to downtown Woodstock and has all of the amenities you could need. We particularly enjoyed the ping-pong table, fireplace, and hot tub. Additionally the host is responsive and cares about you having a comfortable stay. We would definitely stay here again!"
HOT TUB w/ POOL, STREAM on 7 Acres, JUST 2 MINUTES FROM TOWN
Hamptons on the Hudson in South Saugerties
Terrace/patio

Hamptons on the Hudson in South Saugerties

9.8 out of 10, Exceptional, (19)
"Beautiful home and great location . "
Hamptons on the Hudson in South Saugerties
Beautiful new house 3/4 mile from Hunter Mountain
Exterior

Beautiful new house 3/4 mile from Hunter Mountain

9.6 out of 10, Exceptional, (128)
"Great location! Perfect size house for a large family. Had a great time!"
Beautiful new house 3/4 mile from Hunter Mountain
Luxurious Woodstock Home Rental Catskill Mountains Views & Private Retreat
Fridge, microwave, oven, stovetop

Luxurious Woodstock Home Rental Catskill Mountains Views & Private Retreat

10.0 out of 10, Exceptional, (118)
"super easy - we'll be back"
Luxurious Woodstock Home Rental Catskill Mountains Views & Private Retreat
Hidden Charm in Hudson Valley In Dutchess County
Smart TV, fireplace, foosball, table tennis

Hidden Charm in Hudson Valley In Dutchess County

2.0 star property
10.0 out of 10, Exceptional, (15)
"Kristen's home is a wonderful place! Clean and well kept. Was a nice and quiet spot to call home for a few nights. Wouldn't hesitate to book again. "
Hidden Charm in Hudson Valley In Dutchess County
SPECTACULAR Hunter Mountain Views, INCREDIBLE LOCATION-2 minutes to slopes !!
Smart TV, fireplace, computer monitors

SPECTACULAR Hunter Mountain Views, INCREDIBLE LOCATION-2 minutes to slopes !!

9.6 out of 10, Exceptional, (25)
"Had a great 2 night stay. Location is close to Hunter. "
SPECTACULAR Hunter Mountain Views, INCREDIBLE LOCATION-2 minutes to slopes !!
Brand New House with Huge patio overlooks Esopus Creek at Lake Katrine
Private kitchen

Brand New House with Huge patio overlooks Esopus Creek at Lake Katrine

10.0 out of 10, Exceptional, (11)
"Immaculate house beautiful furnishings Very comfortable Everything you need for a relaxing stay Fully equipped"
The price is AEDĀ 731
AEDĀ 1,592 total
includes taxes & fees
14 May - 15 May
Brand New House with Huge patio overlooks Esopus Creek at Lake Katrine
Quaint Cottage w/ Peloton & Sauna near Hiking
Property grounds

Quaint Cottage w/ Peloton & Sauna near Hiking

9.6 out of 10, Exceptional, (18)
"Nice area, cute cottage."
Quaint Cottage w/ Peloton & Sauna near Hiking
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
Exterior

COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!

9.6 out of 10, Exceptional, (25)
"Well located and comfortable "
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
Cozy Retreat w/ Hot Tub, on Sleepy Hollow Lake!
TV, fireplace, books

Cozy Retreat w/ Hot Tub, on Sleepy Hollow Lake!

9.2 out of 10, Wonderful, (23)
"We had a great time staying at this house. It was quiet and relaxing. We would stay again!"
Cozy Retreat w/ Hot Tub, on Sleepy Hollow Lake!
Experience Woodstock charm while staying in a cozy cabin in the woods
Interior

Experience Woodstock charm while staying in a cozy cabin in the woods

9.8 out of 10, Exceptional, (26)
"We had a wonderful long weekend experience ā€” beautiful house, perfect heated pool and a very responsive host. "
Experience Woodstock charm while staying in a cozy cabin in the woods
HUGE KITCHEN 4 Private Acres, 7 Min to Town, WiFi, AC, Fireplace
Exterior

HUGE KITCHEN 4 Private Acres, 7 Min to Town, WiFi, AC, Fireplace

10.0 out of 10, Exceptional, (35)
"Absolutely loved the property and its proximity to the Bearsville Theatre where we had a 2-day concert. We only wish we could have stayed longer than a quick weekend trip!"
HUGE KITCHEN 4 Private Acres, 7 Min to Town, WiFi, AC, Fireplace
Lovely 2 queen size bedroom apt one block from Rough Draft and Uptown Kingston
Terrace/patio

Lovely 2 queen size bedroom apt one block from Rough Draft and Uptown Kingston

10.0 out of 10, Exceptional, (43)
"It was great!"
Lovely 2 queen size bedroom apt one block from Rough Draft and Uptown Kingston
The Best 3-bedroom house in Tivoli
Outdoor pool, a heated pool

The Best 3-bedroom house in Tivoli

The Best 3-bedroom house in Tivoli
Gorgeous Hudson River Waterfrt, 3 Bdrm Pool/Quiet St/Great Views/HITS 2 mile
Terrace/patio

Gorgeous Hudson River Waterfrt, 3 Bdrm Pool/Quiet St/Great Views/HITS 2 mile

2.0 star property
10.0 out of 10, Exceptional, (4)
"Great pool on the river! Loved watching th La ge barges go by! "
Gorgeous Hudson River Waterfrt, 3 Bdrm Pool/Quiet St/Great Views/HITS 2 mile
Cortland by AvantStay | Charming Heritage Estate w/ Private Lake & Pool
Pool

Cortland by AvantStay | Charming Heritage Estate w/ Private Lake & Pool

9.6 out of 10, Exceptional, (17)
"Enjoyed the holiday with family. "
Cortland by AvantStay | Charming Heritage Estate w/ Private Lake & Pool
NEW! Gated 21 Acre Modern Luxury Estate Heated Pool Hot Tub Gym Movie Theater.
Fridge, microwave, oven, stovetop

NEW! Gated 21 Acre Modern Luxury Estate Heated Pool Hot Tub Gym Movie Theater.

9.6 out of 10, Exceptional, (51)
"Beautiful estate, close to town and train station, amazing space overall."
NEW! Gated 21 Acre Modern Luxury Estate Heated Pool Hot Tub Gym Movie Theater.
Where the Broadway Stars Vacation! Private Woodstock getaway & walk to town!
3 bedrooms, iron/ironing board, WiFi, bed sheets

Where the Broadway Stars Vacation! Private Woodstock getaway & walk to town!

10.0 out of 10, Exceptional, (174)
"This was an incredible place to stay for a snowy weekend with the family. The house is huge and and just beautiful. The hosts even had the long driveway plowed and stairs/walkway shoveled for us, would definitely recommend staying here. "
Where the Broadway Stars Vacation! Private Woodstock getaway & walk to town!
Large Barn styled vacation home that fits groups with space to spare.
Miscellaneous

Large Barn styled vacation home that fits groups with space to spare.

10.0 out of 10, Exceptional, (61)
"Another excellent experience stay at this house!"
Large Barn styled vacation home that fits groups with space to spare.
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 Annandale-on-Hudson
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Annandale-on-Hudson

Postcard Cabins Eastern Catskills
Exterior

Postcard Cabins Eastern Catskills

2.0 star property
8.8 out of 10, Excellent, (11)
"We always live these cabins & we've been coming for years!"
The price is AEDĀ 621
AEDĀ 809 total
includes taxes & fees
14 May - 15 May
Postcard Cabins Eastern Catskills
Esopus Creek modern Tiny house Retreat!
Outdoor dining

Esopus Creek modern Tiny house Retreat!

9.6 out of 10, Exceptional, (30)
"Had a fantastic stay for a quick overnight trip to ski."
The price is AEDĀ 569
AEDĀ 897 total
includes taxes & fees
14 May - 15 May
Esopus Creek modern Tiny house Retreat!
Hamptons on the Hudson in South Saugerties
Terrace/patio

Hamptons on the Hudson in South Saugerties

9.8 out of 10, Exceptional, (19)
"Beautiful home and great location . "
Hamptons on the Hudson in South Saugerties
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.