Vacation rentals in Pleasant Valley

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Top-rated vacation rentals in Pleasant Valley

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favorite

Apartment in Staatsburg

5.0 out of 5 average rating, 187 reviews

Through the Woods Farm

Through the Woods Farm is our 23-acre home. Located in northern Dutchess County; we're minutes from Omega, and the villages of Rhinebeck, Red Hook, Millbrook, and Hyde Park. The apartment is ideal for a single guest or a couple; maximum allowed is 4 adults. Each additional adult over 2 adds $50/per night. The second bedroom is small - two adults in it is a tight fit! If you're looking for a peaceful, rural getaway in an immaculate, private apartment that's close to everything, you've found it!

Dec 14 – 21

R2,782 ZAR per night
Guest favorite

Home in Salt Point

4.95 out of 5 average rating, 133 reviews

The Literary Inn-entire house

This 3 bedroom guest house located in Salt Point, Dutchess County in New York State. This quiet private place on a 4 acre property is less than 10 minutes from the Taconic Parkway. The house has cable TV, free wifi, central air and heat, a full kitchen with a dishwasher, a full bathroom, a large deck and private patio. The Hudson Valley is home to Colleges, Museums, historic towns, and great State Parks. There are restaurants offering vegetarian and vegan dishes and super markets are nearby.

Jun 19 – 26

R3,914 ZAR per night
Guest favorite

Cottage in Highland

4.92 out of 5 average rating, 530 reviews

Little Yellow Cottage New Paltz - Kitchen wash/dry

Built over 100 years ago as a chicken hatchery, this gorgeous little gem has been fully restored as a two-story guest cottage. Located in New Paltz just minutes off Exit 18 on I-87 in a very private, quiet, country setting. Only ten minutes from New Paltz Village & SUNY New Paltz and set back on a lightly traveled road for those long summer strolls. You don't even need a car to get here! It's just 12 minutes by taxi from the New Paltz Bus Station or bring your bike up and cycle everywhere!

Aug 4 – 11

R2,958 ZAR per night

Popular amenities for Pleasant Valley vacation rentals

Other great vacation rentals in Pleasant Valley

Guest favorite

Home in New Paltz

4.97 out of 5 average rating, 674 reviews

Victorian Haven

Mar 16 – 23

R2,501 ZAR per night
Guest favorite

Guesthouse in Stanfordville

4.94 out of 5 average rating, 160 reviews

Eco Cottage in the Woods

Aug 17 – 24

R2,205 ZAR per night
Guest favorite

Condo in Poughkeepsie

4.97 out of 5 average rating, 215 reviews

Spacious and stylish entire one bedroom apartment.

Jun 18 – 25

R2,506 ZAR per night
Guest favorite

Home in Kingston

4.97 out of 5 average rating, 269 reviews

This New House

Feb 3 – 10

R2,739 ZAR per night
Guest favorite

Cottage in Clinton Corners

4.94 out of 5 average rating, 155 reviews

brand new (Hudson Valley) Laughing Duck Cottage

Aug 9 – 16

R3,846 ZAR per night
Guest favorite

Apartment in Hyde Park

4.92 out of 5 average rating, 161 reviews

The House By The Pond

Jun 8 – 15

R2,921 ZAR per night
Guest favorite

Loft in Pleasant Valley

5.0 out of 5 average rating, 13 reviews

Be our guest at The Nest!

Feb 3 – 10

R2,410 ZAR per night
Guest favorite

Home in Pleasant Valley

4.97 out of 5 average rating, 72 reviews

Cozy Cape, Centrally Located

Jan 7 – 14

R3,168 ZAR per night
Guest favorite

Apartment in Arlington

4.91 out of 5 average rating, 45 reviews

Arlingtons Finest

Jan 9 – 16

R2,264 ZAR per night
Guest favorite

Home in Pleasant Valley

4.97 out of 5 average rating, 31 reviews

Cosmic Hollow

Aug 1 – 8

R8,578 ZAR per night
Guest favorite

Home in Pleasant Valley

4.82 out of 5 average rating, 74 reviews

Country Cottage: Hudson Valley - Millbrook Area

Sep 30 – Oct 7

R4,374 ZAR per night
Guest favorite

Guesthouse in Poughkeepsie

5.0 out of 5 average rating, 19 reviews

Newly Complete Full Guest Suite!

Dec 11 – 18

R1,832 ZAR per night

Destinations to explore