Guest Houses in Poughkeepsie
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A large steel bridge spanning a wide river, with a cityscape and hills in the background.

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Our top choices for Poughkeepsie guest houses

A house with a porch, a garden with ferns and flowering plants, and a red flowering tree.

A two-story house with a porch, surrounded by lush greenery.

A covered porch with a wicker sofa and a small table, surrounded by lush greenery and ferns.

A cozy room with two wicker chairs, a radiator, and a window with a view of greenery.

1. The Gables of Rhinebeck Inn

The Gables of Rhinebeck Inn

3.0 star property

Rhinebeck Village

9.2 out of 10, Wonderful, (125 reviews)

9.2/10

Wonderful

(125 reviews)

"We enjoyed our stay at The Gables Rhinebeck Inn. We’ll definitely return for another stay.."

maryeliza

$210 nightly

The price is $238

$238 total

Nov 18 - Nov 19

Total with taxes and fees

The Gables of Rhinebeck Inn

A living room with a stone fireplace, blue sofas, a wooden coffee table, and a ceiling fan.

A spacious living room with a high ceiling, a dining area, and a balcony.

A bedroom with a large bed, multiple windows, a ceiling fan, and a dresser.

A wooden deck with a built-in bench and two chairs, surrounded by lush greenery.

2. Moondance Ridge Bed & Breakfast

Moondance Ridge Bed & Breakfast

3.0 star property

New Paltz

9.4 out of 10, Exceptional, (122 reviews)

9.4/10

Exceptional

(122 reviews)

"Went for the weekend with my girlfriend, was an amazing trip. The room was very cozy and comfortable. The whole house was beautiful and clean. The amenities was excellent. Definitely recommend this and definitely will book again very soon."

Nicholas

$273 nightly

The price is $306

$306 total

Dec 15 - Dec 16

Total with taxes and fees

Moondance Ridge Bed & Breakfast

A two-story house with a porch, white railings, and a blue door.

A modern kitchen with grey cabinetry, a stainless steel refrigerator, a built-in oven, and a coffee maker.

A modern living room with a sofa, coffee table, and a dining area with a table and chairs.

A two-story house with a wrap-around porch, multiple windows with shutters, and a steeply pitched roof.

3. Station Inn Pawling

Station Inn Pawling

3.0 star property

Pawling

9.2 out of 10, Wonderful, (218 reviews)

9.2/10

Wonderful

(218 reviews)

"Terrific property with great restaurants in walking distance in charming Pawling village."

Sheila

$146 nightly

The price is $165

$165 total

Dec 14 - Dec 15

Total with taxes and fees

Station Inn Pawling

A modern bedroom with a large bed, a red sofa, a fireplace, and a television.

A room with a long wooden table, multiple chairs, a sofa, and large windows offering a forest view.

A window with a view of a forested area, a small potted plant, and a black kettle on the windowsill.

A wooden deck with wicker chairs and a small table, overlooking a forested area.

4. The Harlow House

The Harlow House

2.0 star property

Rhinebeck

8.8 out of 10, Excellent, (24 reviews)

8.8/10

Excellent

(24 reviews)

"Great place"

Robert

$187 nightly

The price is $211

$211 total

Nov 22 - Nov 23

Total with taxes and fees

The Harlow House

A modern house with a wooden deck, a fire pit, and a covered outdoor seating area.

A two-story house with a porch, a sign for 'The Herwood Inn', and a well-maintained lawn.

A modern bedroom with a bed, a small desk, and a kitchenette area.

A modern kitchen with a wooden island, black cabinets, and a built-in refrigerator. There are hanging plants, a coffee machine, and shelves with dishes and utensils.

5. The Herwood Inn

The Herwood Inn

4.0 star property

Woodstock

9.6 out of 10, Exceptional, (148 reviews)

9.6/10

Exceptional

(148 reviews)

"Wonderful experience! The room was beautiful and equipped with everything you could think of. We had such a lovely,relaxing stay."

Diana

$351 nightly

The price is $394

$394 total

Dec 14 - Dec 15

Total with taxes and fees

The Herwood 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.

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Poughkeepsie and related destinations

Poughkeepsie
Newburgh
Macon
Somerset
Parsippany

Stroll along the elevated Walkway Over the Hudson for spectacular river views and a glimpse of the Catskill Mountains. Vassar College's art museum and the historic Bardavon Opera House offer cultural experiences worth planning your visit around.

See all hotels in Poughkeepsie

Top reviews in Poughkeepsie

Moondance Ridge Bed & Breakfast

New Paltz

10/10 Excellent

Absolutely wonderful experience 💕 You are really doing yourself a huge disservice if you choose to stay elsewhere! One of the most peaceful places on earth!! ✌️💕

Claire

Reviewed September 8, 2024Reviewed September 8, 2024

Moondance Ridge Bed & Breakfast

The Gables of Rhinebeck Inn

Rhinebeck Village

10/10 Excellent

This was the most beautiful place to stay for a quiet break. Thank you!

Rebecca

Reviewed August 13, 2026Reviewed August 13, 2026

The Gables of Rhinebeck Inn

The Harlow House

Rhinebeck

10/10 Excellent

Great place

Robert

Reviewed October 21, 2026Reviewed October 21, 2026

The Harlow House

The Herwood Inn

Woodstock

10/10 Excellent

Such a cute spot! Space had fun design and spacious accommodations!

Laura

Reviewed February 8, 2026Reviewed February 8, 2026

The Herwood Inn

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Search Guest Houses in Poughkeepsie

Bundle & Save

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Upfront pricing

Check prices for these dates

Our top choices for Poughkeepsie guest houses

1. The Gables of Rhinebeck Inn

2. Moondance Ridge Bed & Breakfast

3. Station Inn Pawling

4. The Harlow House

5. The Herwood Inn

Poughkeepsie and related destinations

Top reviews in Poughkeepsie

Moondance Ridge Bed & Breakfast

10/10 Excellent

Explore a world of travel with Expedia