Poughkeepsie Rentals

Close

Enter dates for more accurate prices

Payment Protection
Your payment for this rental is protected when you pay through FlipKey. Learn more

77 Houses

16

Charming Brick House -Hudson Valley

New York / Poughkeepsie

Poughkeepsie house

3 7 2 nights min

  • 3 bedrooms
  • sleeps 7
  • 2 nights min
  • Child Friendly
  • Pet Friendly

Price per night from

$301

Price per night from

$301

Great rentals within 20 miles that match your search

Distance approx 18.07 km from Poughkeepsie

32

Lake House with Indoor Spa, 1 hour from Manhattan

New York / Carmel

Carmel house

3 6 2 nights min

  • 3 bedrooms
  • sleeps 6
  • 2 nights min
  • Child Friendly

Price per night from

$201

Price per night from

$201

Distance approx 19.49 km from Poughkeepsie

(3) Very Good 

43

Stony Mountain House

Catskill Region / Pine Bush

Pine Bush house

5 16 3 nights min

  • 5 bedrooms
  • sleeps 16
  • 3 nights min
  • Child Friendly

Price per night from

$361

Responds fast!
avg. 2 hours 34 minutes

Price per night from

$361

Distance approx 19.16 km from Poughkeepsie

19

Harley's Hideaway, A Relaxing Escape

New York / Stanfordville

Stanfordville apartment

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Nearest beach 20 mi
  • Air conditioning
  • Private garden

Price per night from

$141

Price per night from

$141

Distance approx 14.85 km from Poughkeepsie

(11) Very Good 

17

Calder's Cottage in the historic artistic Rondout

New York / Kingston

Kingston house

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Nearest beach 2 mi
  • Child Friendly
  • Car not necessary
“Charming Historic House and Great Hosts” We rented Calder's Cottage for a trip with friends to visit nearby historic sites. The house is a delight...fresh and comfortable in every respect. The hosts made it even better with their warmth, helpful inf
…see more

Price per night from

$175

Price per night from

$175

Distance approx 16.97 km from Poughkeepsie

28

Hudson Valley Cabin - Romantic & Secluded Log Cabin with Private Lake - 85 acres

New York / Stanfordville

Stanfordville log cabin

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min

Price per night from

$226

Price per night from

$226

Distance approx 13.35 km from Poughkeepsie

26

Beautiful Streamside Cottage in Dutchess County

New York / Clinton Corners

Clinton Corners house

2 8 2 nights min

  • 2 bedrooms
  • sleeps 8
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 3 mi
  • Child Friendly

Price per night from

$251

Price per night from

$251

Distance approx 17.15 km from Poughkeepsie

35

THE STABLES IN THE CARRIAGE HOUSE

New York / Kingston

Kingston villa

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Nearest beach 5 mi
  • Car not necessary
  • Air conditioning

Price per night from

$226

Price per night from

$226

Distance approx 10.17 km from Poughkeepsie

(1) Excellent 

44

for the creative spirit, lightfilled loft house

New York / Ulster Park

Ulster Park studio

Studio 3 2 nights min

  • Studio
  • sleeps 3
  • 2 nights min
  • Child Friendly

Price per night from

$250

Responds fast!
avg. 1 hour 54 minutes

Price per night from

$250

Distance approx 8.88 km from Poughkeepsie

(2) Excellent 

22

New Paltz meets Cape May

New York / New Paltz

New Paltz house

4 8 2 nights min

  • 4 bedrooms
  • sleeps 8
  • 2 nights min
  • Ski
  • Child Friendly
  • Air conditioning

Price per night from

$651

Price per night from

$651

Distance approx 12.98 km from Poughkeepsie

38

Amazing Holiday Home

New York / New Paltz

New Paltz house

3 8 3 nights min

  • 3 bedrooms
  • sleeps 8
  • 3 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Price per night from

$852

Price per night from

$852

Distance approx 12.09 km from Poughkeepsie

22

Woodland House - sleeps 10 in luxury

New York / Rhinebeck

Rhinebeck house

5 10 2 nights min

  • 5 bedrooms
  • sleeps 10
  • 2 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$600

Price per night from

$600

Distance approx 14.72 km from Poughkeepsie

(2) Very Good 

12

Keith's Classic Film Retreat

New York / Newburgh

Newburgh b and b

2 4 1 night min

  • 2 bedrooms
  • sleeps 4
  • 1 night min
  • Child Friendly
  • Car not necessary
  • Air conditioning

Price per night from

$100

Price per night from

$100

Distance approx 12.23 km from Poughkeepsie

19

Converted Barn on 5+ Acres. WiFi & Serenity.

New York / Clinton Corners

Clinton Corners house

4 6 7 nights min

  • 4 bedrooms
  • sleeps 6
  • 7 nights min
  • Child Friendly

Price per night from

$280

Price per night from

$280

Distance approx 10.2 km from Poughkeepsie

(5) Very Good 

11

Earth Berm House at Terra Casa Retreat Center

New York / Plattekill

Plattekill house

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Child Friendly

Price per night from

$286

Price per night from

$286

Distance approx 8.16 km from Poughkeepsie

20

Phillie's Country Comfort Space -

New York / New Paltz

New Paltz b and b

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Air conditioning
  • Private garden

Price per night from

$116

Price per night from

$116

Distance approx 19.85 km from Poughkeepsie

(8) Excellent 

21

Enchanting Cottage In The Woods

New York / Accord

Accord cottage

3 8 2 nights min

  • 3 bedrooms
  • sleeps 8
  • 2 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly
“Peaceful Getaway” A group of childhood friends, our spouses, and my young child just completed a visit to this lovely cottage. We had a wonderful time in the peaceful and beautiful Catskills -- hiked at Minnewaska State park, biked on the O&W; Rail Tr
…see more

Price per night from

$386

Price per night from

$386

Distance approx 3.51 km from Poughkeepsie Show on Map

57

Hudson Valley Villa - Modern Masterpiece Cantilevered Over Hudson River Bluff

New York / Highland

Highland house

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Nearest beach 14 mi
  • Swimming pool
  • Child Friendly

Price per night from

$1,197

Responds fast!
avg. 24 minutes

Price per night from

$1,197

Distance approx 16.39 km from Poughkeepsie

14

Antique Stone House

New York / Kingston

Kingston b and b

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Child Friendly

Price per night from

$151

Price per night from

$151

Distance approx 15.03 km from Poughkeepsie

(2) Excellent 

23

Church Des Artistes

New York / Kingston

Kingston villa

4 14 3 nights min

  • 4 bedrooms
  • sleeps 14
  • 3 nights min
  • Child Friendly
  • Air conditioning
  • Pet Friendly
“Wonderful!” This was one of the most unusual places we've ever stayed- a renovated old church, at the same time classic, modern, absolutely spotless, warm, bright, cozy and if you appreciate the arts you are in for a treat as both Julie and Peter are
…see more

Price per night from

$826

Responds fast!
avg. 1 hour 8 minutes

Price per night from

$826

Distance approx 16.35 km from Poughkeepsie

(4) Excellent 

6

Comfy Room in Private Home, Ideal Location, Sauna!

New York / Kingston

Kingston room

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$60

Responds fast!
avg. 1 hour 52 minutes

Price per night from

$60

Distance approx 15.93 km from Poughkeepsie

11

Two Kings House–Historic-Modern Victorian in Uptown Kingston

New York / Kingston

Kingston house

3 7 2 nights min

  • 3 bedrooms
  • sleeps 7
  • 2 nights min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$150

Price per night from

$150

Distance approx 16.35 km from Poughkeepsie

25

Elegant 3BR. in the Heart of Historic Kingston.

New York / Kingston

Kingston apartment

3 8 2 nights min

  • 3 bedrooms
  • sleeps 8
  • 2 nights min
  • Nearest beach 8 mi
  • Ask about children
  • Car not necessary

Price per night from

$246

Price per night from

$246

Distance approx 12.64 km from Poughkeepsie

14

Modern Cottage With Deck & Hot Tub in Rosendale

New York / Kingston

Kingston log cabin

2 1 night min

  • sleeps 2
  • 1 night min
  • Air conditioning
  • Private garden

Price per night from

$80

Responds fast!
avg. 52 minutes

Price per night from

$80

Distance approx 13.53 km from Poughkeepsie

(6) Excellent 

33

Beacon Nook, escape from the big city

New York / Beacon

Beacon house

3 7 3 nights min

  • 3 bedrooms
  • sleeps 7
  • 3 nights min
  • Child Friendly
  • Pet Friendly

Price per night from

$251

Price per night from

$251

Distance approx 9.12 km from Poughkeepsie

20

Perfect New Paltz Location

New York / New Paltz

New Paltz house

3 8 2 nights min

  • 3 bedrooms
  • sleeps 8
  • 2 nights min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$301

Price per night from

$301

Distance approx 17.98 km from Poughkeepsie

(2) Very Good 

35

Guesthouse at 30s Bungalow Colony with 5.5 acres Al yours!

Catskill Region / Kerhonkson

Kerhonkson house

2 7 2 nights min

  • 2 bedrooms
  • sleeps 7
  • 2 nights min
  • Car not necessary
  • Air conditioning
  • Pet Friendly

Price per night from

$121

Price per night from

$121

Distance approx 11.13 km from Poughkeepsie

(2) Excellent 

26

romantig house at magical lake

New York / Ulster Park

Ulster Park house

2 5 2 nights min

  • 2 bedrooms
  • sleeps 5
  • 2 nights min
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$250

Responds fast!
avg. 1 hour 54 minutes

Price per night from

$250

Distance approx 6.36 km from Poughkeepsie

14

House on Top of the Hill

New York / Marlboro

Marlboro house

3 5 7 nights min

  • 3 bedrooms
  • sleeps 5
  • 7 nights min
  • Suitable for children age 5+
  • Air conditioning

Price per night from

$101

Responds fast!
avg. 2 hours 39 minutes

Price per night from

$101

Distance approx 16.38 km from Poughkeepsie

13

The Wiltwick

New York / Kingston

Kingston apartment

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Child Friendly
  • Car not necessary
  • Air conditioning

Price per night from

$101

Price per night from

$101

Distance approx 14.94 km from Poughkeepsie

59

Just steps from the Rondout waterfront, shops and restaurants.

New York / Kingston

Kingston apartment

1 4 1 night min

  • 1 bedroom
  • sleeps 4
  • 1 night min
  • Child Friendly
  • Car not necessary
  • Air conditioning

Price per night from

$126

Price per night from

$126

Distance approx 17.94 km from Poughkeepsie

(1) Excellent 

31

Private Lakefront & Pool DeeLuxGlamping. NYC Getaway

New York / Pawling

Pawling camper van

2 8 1 night min

  • 2 bedrooms
  • sleeps 8
  • 1 night min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$158

Price per night from

$158

Distance approx 14.75 km from Poughkeepsie

(4) Excellent 

12

DeMew House

New York / Kingston

Kingston house

1 4 2 nights min

  • 1 bedroom
  • sleeps 4
  • 2 nights min

Price per night from

$176

Price per night from

$176

Distance approx 12.45 km from Poughkeepsie

24

Charming Hudson Valley Studio - Walk to Downtown!

New York / Fishkill

Fishkill studio

Studio 2 min stay varies

  • Studio
  • sleeps 2
  • min stay varies
  • Child Friendly
  • Air conditioning

Price per night from

$116

Responds fast!
avg. 10 minutes

Price per night from

$116

Distance approx 15.97 km from Poughkeepsie

32

Summer or Summer Monthly Swimming Lake Rhinebeck Oasis

New York / Rhinebeck

Rhinebeck house

3 8 30 nights min

  • 3 bedrooms
  • sleeps 8
  • 30 nights min
  • Child Friendly
  • Pet Friendly

Price per night from

$234

Price per night from

$234

Distance approx 9.74 km from Poughkeepsie

18

1880s HUDSON VALLEY NEW PALTZ CATSKILLS FARMHOUSE BEAUTIFULLY FURNiSHED POOL

New York / Rifton

Rifton house

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Child Friendly

Price per night from

$451

Price per night from

$451

Distance approx 13.53 km from Poughkeepsie

19

ROMANTIC GETAWAY COTTAGE ON WATER

New York / Beacon

Beacon cottage

3 8 2 nights min

  • 3 bedrooms
  • sleeps 8
  • 2 nights min
  • Child Friendly
  • Car not necessary
  • Air conditioning

Price per night from

$226

Responds fast!
avg. 2 hours 2 minutes

Price per night from

$226

Distance approx 4.7 km from Poughkeepsie Show on Map

(12) Excellent 

18

Hudson Valley 40 Acres With Lake And Hiking

New York / Highland

Highland house

4 12 2 nights min

  • 4 bedrooms
  • sleeps 12
  • 2 nights min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$551

Responds fast!
avg. 29 minutes

Price per night from

$551