Poughkeepsie Vacation Rentals

    price find illustration

    Upfront pricing

    Our total price for your stay includes taxes and fees
    deals illustration

    Treat yourself

    Save 10% or more on over 100,000 hotels worldwide with Member Prices
    Learn about One Key
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
Aug 5 - Aug 6
Tomorrow
Aug 6 - Aug 7
This weekend
Aug 8 - Aug 10
Next weekend
Aug 15 - Aug 17

Vacation Rentals in Poughkeepsie

1 Br Private Victorian Apt in Convenient City Location on Half Acre Sleeps 4
Relax in this stylish living room with a comfortable sofa, coffee table, and armchair, surrounded by tasteful art and a beautiful view.

1 Br Private Victorian Apt in Convenient City Location on Half Acre Sleeps 4

2.0 star property
9.6 out of 10, Exceptional, (7)
"Gary is a great host and provides a wonderful experience. He is the best and it was a very nice stay. Best host I have had before."
$174 nightly
The price is $204
Aug 6 - Aug 7
Total includes taxes and fees
1 Br Private Victorian Apt in Convenient City Location on Half Acre Sleeps 4
The Farm at Hyde Park
Set amidst lush greenery and mature trees, this charming building features a steeply pitched roof and a brick facade.

The Farm at Hyde Park

9.8 out of 10, Exceptional, (74)
"We were visiting the Culinary Institute highly recommend it."
The Farm at Hyde Park
Streamside Cottage Half Mile to Town of Woodstock
Property grounds

Streamside Cottage Half Mile to Town of Woodstock

10.0 out of 10, Exceptional, (246)
"A beautiful quiet setting! "
$301 nightly
The price is $337
Sep 2 - Sep 3
Total includes taxes and fees
Streamside Cottage Half Mile to Town of Woodstock
Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views
Relax on the serene deck, surrounded by bare trees and a frozen lake.

Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views

10.0 out of 10, Exceptional, (301)
"The lake views at this house are absolutely worth the trip and the money. It's a beautiful spot. And the host, Don, is super responsive, thoughtful and accommodating. Highly recommend!"
$459 nightly
The price is $542
Aug 10 - Aug 11
Total includes taxes and fees
Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Relax in this serene outdoor seating area with a covered patio overlooking a lush garden.

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

9.8 out of 10, Exceptional, (27)
"Perfect for small family stay over for a wedding ! "
$296 nightly
The price is $335
Aug 31 - Sep 1
Total includes taxes and fees
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Junebug Cottage: peace, love and privacy a short walk to Woodstock village green
Set amidst a serene wooded area, this two-story house offers a retreat with a well-manicured lawn and a small deck.

Junebug Cottage: peace, love and privacy a short walk to Woodstock village green

10.0 out of 10, Exceptional, (71)
"We were in Woodstock for a wedding. Junebug Cottage was perfect for our stay! "
Junebug Cottage: peace, love and privacy a short walk to Woodstock village green
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
Enjoy cooking in this well-equipped kitchen with a central island, stainless steel stove, and ample counter space.

Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.

10.0 out of 10, Exceptional, (85)
"We loved our stay. It was great for a family Thanksgiving"
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
7BR Monroe Getaway: Pool, Hot Tub, & Huge Living Space
Fridge, microwave, oven, stovetop

7BR Monroe Getaway: Pool, Hot Tub, & Huge Living Space

8.0 out of 10, Very Good, (1)
$1,712 nightly
The price is $1,937
Aug 28 - Aug 29
Total includes taxes and fees
7BR Monroe Getaway: Pool, Hot Tub, & Huge Living Space
Where the Broadway Stars Vacation! Private Woodstock getaway & walk to town!
Enjoy a peaceful forest view from the large window, featuring a comfortable bed below.

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

10.0 out of 10, Exceptional, (176)
"Loved our stay and the house. Everything was wonderful. I will say it was a little farther than 'a walk into town' and we did Uber everywhere. Everything at the house was great - nice relaxing spot!!"
Where the Broadway Stars Vacation! Private Woodstock getaway & walk to town!
Esopus Creek modern Tiny house Retreat!
Enjoy a romantic dinner for two on this deck with a beautiful floral arrangement and a bottle of wine.

Esopus Creek modern Tiny house Retreat!

9.6 out of 10, Exceptional, (44)
"4 of us stayed for a fishing trip and had a blast. Nice place at a reasonable price. Would stay again. "
$209 nightly
The price is $234
Aug 17 - Aug 18
Total includes taxes and fees
Esopus Creek modern Tiny house Retreat!
Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!
Enjoy a peaceful lakeside retreat with a barbecue grill and comfortable seating area.

Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!

9.0 out of 10, Wonderful, (18)
"We really enjoyed our stay. The house is walking distance from the lake and a good break for anyone trying to escape the bustle of NYC. The house was very clean and we felt safe and comfortable here’s the outdoor fire pit was a very nice touch."
Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!
Minutes to Saugerties & HITS Horse show. Above garage w/ own private entrance.
Enjoy cooking in this well-equipped kitchen with a central island, sink, and stove.

Minutes to Saugerties & HITS Horse show. Above garage w/ own private entrance.

2.0 star property
$206 nightly
The price is $231
Aug 6 - Aug 7
Total includes taxes and fees
Minutes to Saugerties & HITS Horse show. Above garage w/ own private entrance.
Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks
Enjoy cooking in this well-equipped kitchen with a large island, oven, and stainless steel range hood.

Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks

2.0 star property
9.8 out of 10, Exceptional, (11)
"A group of girlfriends stayed for a 2 night visit. Everything was just as listed, the home was in the perfect location, well stocked, and beautiful inside. We would definitely return again. "
$519 nightly
The price is $526
Aug 6 - Aug 7
Total includes taxes and fees
Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks
Charming cottage with lake access, wood burning fire place, and WiFi
Relax in this inviting living room with a sofa, dresser, and small table.

Charming cottage with lake access, wood burning fire place, and WiFi

2.0 star property
9.0 out of 10, Wonderful, (7)
"Oriana was awesome and I look forward to staying there again."
Charming cottage with lake access, wood burning fire place, and WiFi
Ultimate Lakeside Getaway on 5 Acres - Private Dock, Kayaks, Fire Pit - Sleeps 9
Terrace/patio

Ultimate Lakeside Getaway on 5 Acres - Private Dock, Kayaks, Fire Pit - Sleeps 9

9.6 out of 10, Exceptional, (8)
Ultimate Lakeside Getaway on 5 Acres - Private Dock, Kayaks, Fire Pit - Sleeps 9
The Studio at the Inn at High Falls
Situated in a lush forest, this cabin offers a serene retreat with a symmetrical facade and a well-manicured lawn.

The Studio at the Inn at High Falls

8.0 out of 10, Very Good, (26)
"I had a great stay here, it’s just as listed; simple but has everything that I needed, check in was easy, communication was good, and bed was comfortable!"
$240 nightly
The price is $268
Aug 6 - Aug 7
Total includes taxes and fees
The Studio at the Inn at High Falls
New Breathtaking Catskill Retreat with Views and Hot Tub, The Nest Retreat in Woodstock Catskill
Relax in a spacious bedroom with a large bed, bedside table, and lamp, offering a view of the balcony and adjacent room.

New Breathtaking Catskill Retreat with Views and Hot Tub, The Nest Retreat in Woodstock Catskill

10.0 out of 10, Exceptional, (18)
"Really enjoyed this place . Very clean , beautiful views, close to Woodstock town !"
New Breathtaking Catskill Retreat with Views and Hot Tub, The Nest Retreat in Woodstock Catskill
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Stroll through a serene residential setting surrounded by a lush lawn, a tree, and a picturesque bridge.

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

9.8 out of 10, Exceptional, (118)
"Nice view on the top of the mountain….I admired the river with the bridge and the surroundings until late in the night. The accommodation was excellent, we had everything we needed.… we are thinking of coming back sometime…."
$288 nightly
The price is $326
Aug 6 - Aug 7
Total includes taxes and fees
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
A Spectacular 50 Mile View of the Hudson Valley in all seasons
Perched on a rocky outcrop, this historic lighthouse offers stunning views of the surrounding waters.

A Spectacular 50 Mile View of the Hudson Valley in all seasons

9.8 out of 10, Exceptional, (89)
"This was exactly what we needed for a quick getaway after Christmas. Myra & Jerry were fantastic hosts, and the accommodations were cozy. We'd definitely come back. Thanks Myra & Jerry!"
A Spectacular 50 Mile View of the Hudson Valley in all seasons
THE ARTIST’S LOFT- Peaceful 1-bedroom apartment in lovely Red Hook with AC, WiFi
Cozy apartment with a large bed, flat-screen TV, and a window with blinds.

THE ARTIST’S LOFT- Peaceful 1-bedroom apartment in lovely Red Hook with AC, WiFi

10.0 out of 10, Exceptional, (2)
"loved the discovery of Rose Hill Farm and its close proximity to Greig Farm, Tivoli, and the town of Red Hook."
$215 nightly
The price is $243
Aug 6 - Aug 7
Total includes taxes and fees
THE ARTIST’S LOFT- Peaceful 1-bedroom apartment in lovely Red Hook with AC, WiFi
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Poughkeepsie Hotel Reviews

Americas Best Value Inn New Paltz

Americas Best Value Inn New Paltz

10/10 Excellent
"Mattresses are a bit bouncy but what are you gonna do lol staff was wonderful. We were comfortable. "
Shannon 1-night trip
Posted 1 day ago
Americas Best Value Inn New Paltz

Frequently asked questions

Are there vacation rentals in Poughkeepsie?

Yes, we offer vacation rentals in Poughkeepsie near Mid-Hudson Civic Center, or you can choose a secluded option if you'd like a relaxing place to stay. Visitors like the college campus and scenic riverfront in Poughkeepsie. While you're in the area, you can also enjoy the top-notch restaurants and entertainment venues.

What's the top vacation rental in Poughkeepsie?

The Farm at Hyde Park: This vacation home rental near Poughkeepsie is located in a rural location and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many vacation rentals are there in Poughkeepsie?

Expedia has 22 vacation rentals for your stay in Poughkeepsie.

What can I see and do in Poughkeepsie?

Mid-Hudson Civic Center and McCann Ice Arena are a couple of family-friendly sights, whereas cultural attractions include Bardavon 1869 Opera House and Locust Grove. Other places in town to visit include Mid-Hudson Bridge and Poughkeepsie Bridge.

What are vacation rentals like in Poughkeepsie?

Vacation rentals are private accommodations you can reserve for several days or more in Poughkeepsie. Vacation rentals feature extras such as patios, hot tubs, and fire pits so you'll have everything you want. If you're concerned about a sanitized environment, vacation rentals can provide a sense of security away from shared hotel elevators and busy reception areas while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive option for a family trip.