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Discover 1,361 Roundout hotels and places to stay, with room rates, reviews, and availability. Most hotels are fully refundable.

Kingston Carriage House

4.0 star property
9.2 out of 10, Wonderful, (19)
"one of the best places we’ve stayed at! the poet’s loft is a cozy and quiet two-room suite with two bathrooms. a simple luxury to be enjoyed."
$336 nightly
The price is $376
Aug 3 - Aug 4
Total includes taxes and fees
Kingston Carriage House

Millbrook Country House Bed & Breakfast

4.0 star property
9.0 out of 10, Wonderful, (77)
"Gracious host and great breakfast "
$198 nightly
The price is $224
Aug 12 - Aug 13
Total includes taxes and fees
Millbrook Country House Bed & Breakfast

Inn at Pine Plains

3.5 star property
9.8 out of 10, Exceptional, (287)
"Beautiful place. Accomadating staff. A lovely place to stay"
$255 nightly
The price is $288
Jul 28 - Jul 29
Total includes taxes and fees
Inn at Pine Plains

Jenny's Country Manor

2.0 star property
7.6 out of 10, Good, (130)
"The paint job could be redone and the stair are a bit hazardous. The bath facilities could be improved."
$140 nightly
The price is $158
Jul 28 - Jul 29
Total includes taxes and fees
Jenny's Country Manor

it's a good thing

4.5 star property
8.6 out of 10, Excellent, (17)
"Wonderful stay and wonderful hosts! "
$146 nightly
The price is $166
Aug 2 - Aug 3
Total includes taxes and fees
it's a good thing

The Harlow House

2.0 star property
10.0 out of 10, Exceptional, (18)
"Amazingly clean, comfortable and conveniently close to the Omega Institute! We loved our stay and how close it was to the Brian Weiss workshop weekend."
$209 nightly
The price is $237
Aug 25 - Aug 26
Total includes taxes and fees
The Harlow House

Quality Inn Poughkeepsie

2.5 star property
7.8 out of 10, Good, (380)
"Property safe and clean nice place to go for a weekend getaway"
$103 nightly
The price is $119
Jul 30 - Jul 31
Total includes taxes and fees
Quality Inn Poughkeepsie

The Heartwood

2.5 star property
9.8 out of 10, Exceptional, (174)
"Very neat and nice staff and right location."
$189 nightly
The price is $220
Aug 3 - Aug 4
Total includes taxes and fees
The Heartwood

Holiday Inn Express Poughkeepsie by IHG

2.5 star property
8.6 out of 10, Excellent, (1016)
"I would stay here again. It's a good hotel, easy in and out access to highway, close to attractions, clean. "
$105 nightly
The price is $122
Aug 3 - Aug 4
Total includes taxes and fees
Holiday Inn Express Poughkeepsie by IHG

Residence Inn by Marriott Poughkeepsie

3.0 star property
8.8 out of 10, Excellent, (602)
"Pool and hot tub were great for families. "
$152 nightly
The price is $177
Aug 18 - Aug 19
Total includes taxes and fees
Residence Inn by Marriott Poughkeepsie

Courtyard by Marriott Poughkeepsie

3.0 star property
8.8 out of 10, Excellent, (1002)
"It a nice relaxing place to stay"
$110 nightly
The price is $124
Aug 18 - Aug 19
Total includes taxes and fees
Courtyard by Marriott Poughkeepsie

Home2 Suites By Hilton Poughkeepsie

3.0 star property
9.4 out of 10, Exceptional, (297)
"This day was awesome everything was inwalking distance it was clean quiet and I would recommend the people I know to stay there awesome"
$135 nightly
The price is $157
Aug 3 - Aug 4
Total includes taxes and fees
Home2 Suites By Hilton Poughkeepsie

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."
$232 nightly
The price is $272
Jul 28 - Jul 29
Total includes taxes and fees
1 Br Private Victorian Apt in Convenient City Location on Half Acre Sleeps 4

2Br Private Victorian Apartment in City Location on Half Acre Sleeps 5

2.0 star property
10.0 out of 10, Exceptional, (3)
"My friends and I rented this property for a long girls weekend to attend an event in the area. We liked the historical aspect of the property and Gary was an excellent host. His banana bread was amazing! We would definitely stay again. "
$290 nightly
The price is $340
Jul 28 - Jul 29
Total includes taxes and fees
2Br Private Victorian Apartment in City Location on Half Acre Sleeps 5

Inn at Bellefield / Hyde Park, Residence Inn by Marriott

3.0 star property
9.6 out of 10, Exceptional, (367)
"We had an excellent stay. Location was perfect. "
$161 nightly
The price is $182
Aug 18 - Aug 19
Total includes taxes and fees
Inn at Bellefield / Hyde Park, Residence Inn by Marriott

Quality Inn Hyde Park Poughkeepsie North

2.5 star property
8.0 out of 10, Very Good, (1012)
"Easy access to roads and nearby sites."
$80 nightly
The price is $91
Aug 17 - Aug 18
Total includes taxes and fees
Quality Inn Hyde Park Poughkeepsie North

Inn the Woods Bed and Breakfast

3.5 star property
9.8 out of 10, Exceptional, (127)
"We had a very relaxed time there. Nice room and you feel like you are living in the woods. He makes a great breakfast. it was quiet and we could sleep well. We will go back."
$174 nightly
The price is $197
Jul 29 - Jul 30
Total includes taxes and fees
Inn the Woods Bed and Breakfast

Roosevelt Inn of Hyde Park

2.5 star property
9.4 out of 10, Exceptional, (520)
"Nice property, staff very professional and great breakfast "
$143 nightly
The price is $162
Aug 3 - Aug 4
Total includes taxes and fees
Roosevelt Inn of Hyde Park

Journey Inn Bed & Breakfast

4.0 star property
9.6 out of 10, Exceptional, (324)
"Great place"
$224 nightly
The price is $253
Jul 31 - Aug 1
Total includes taxes and fees
Journey Inn Bed & Breakfast

The Gables of Rhinebeck Inn

3.0 star property
9.2 out of 10, Wonderful, (106)
"Large clean room. Comfy beds. Great location. Lovely stay!!"
$255 nightly
The price is $289
Jul 28 - Jul 29
Total includes taxes and fees
The Gables of Rhinebeck Inn
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.

Where to stay in Roundout

Find the best Roundout areas and neighborhoods for the activities you enjoy most.
Hillside map

Hillside

When in Hillside, you can plan a visit to Esopus Creek and Ulster Performing Arts Center, some noteworthy sights in the nearby area.

Kingston Stockade District map

Kingston Stockade District

You'll enjoy the churches and spas in Kingston Stockade District. You might want to make time for a stop at Senate House State Historic Site or Birch Body Care.

Stockade Historic District map

Stockade Historic District

If you're spending some time in Stockade Historic District, Senate House State Historic Site and Birch Body Care are top sights worth seeing.

Top Roundout Hotel Reviews