Dutchess County Holiday Rentals

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Top Cities in Dutchess County

Franklin D. Roosevelt Presidential Library and Museum featuring heritage elements and heritage architecture
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Hyde Park

Hyde Park
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Millbrook

Millbrook

Top Holiday Rentals Destinations in Dutchess County

The Farm at Hyde Park
Exterior

The Farm at Hyde Park

9.8 out of 10, Exceptional, (63)
"Quiet spot out of the city but not too far from Hudson Valley sites. Large vaulted space, fresh eggs from the hen house next door, sky full of stars at night. Great host!"
The Farm at Hyde Park
Micosta Leisure Inn
Balcony

Micosta Leisure Inn

3.0 star property
9.2 out of 10, Wonderful, (89)
"Fantastic place to stay! So homey, comfortable, and peaceful. Steven was a fabulous host, and his property is wonderful - in a beautiful garden. The room is large and beyond well equipped. No reason to pay more to stay downtown Hudson. We’re on a month-long New England road trip, and this has been our favorite stay! "
The price is NZ$212
includes taxes & fees
5 Dec - 6 Dec
Micosta Leisure Inn
Streamside Cottage Half Mile to Town of Woodstock
Aerial view

Streamside Cottage Half Mile to Town of Woodstock

10.0 out of 10, Exceptional, (224)
"Place was a perfect place to unwind. Very clean and Jane was very communicative!"
The price is NZ$548
includes taxes & fees
27 Nov - 28 Nov
Streamside Cottage Half Mile to Town of Woodstock
Lakehouse, Private Beach, Kayaks, FirePit, Gym, Movie Room, Pool Table, Air Hock
On the beach, sun-loungers

Lakehouse, Private Beach, Kayaks, FirePit, Gym, Movie Room, Pool Table, Air Hock

9.6 out of 10, Exceptional, (74)
"The house is as advertised. Good amount of room. The host was pretty communicative. No complaints from the property. Just wish they had a bigger table for group dinners"
Lakehouse, Private Beach, Kayaks, FirePit, Gym, Movie Room, Pool Table, Air Hock
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
Exterior

'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY

8.2 out of 10, Very good, (42)
"We had a great time at the cabin! It was the perfect escape from the city. The view was gorgeous, and the cabin had everything we needed. We also tried to use the canoe but the padlock is stuck, it might be rusted/need to be replaced. Otherwise everything was perfect!"
The price is NZ$247
includes taxes & fees
24 Nov - 25 Nov
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Property grounds

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

9.8 out of 10, Exceptional, (105)
"Super cozy apartment with a beautiful view. Very welcoming host and a great place for a short stay near Bear Mountain. "
The price is NZ$423
includes taxes & fees
30 Nov - 1 Dec
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Cozy Relaxing Retreat in Saugerties, NY
Exterior

Cozy Relaxing Retreat in Saugerties, NY

10.0 out of 10, Exceptional, (42)
"Secluded house very quiet surrounding, owner was very quick to respond "
Cozy Relaxing Retreat in Saugerties, NY
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
Interior

The Freeman - Newly Renovated 14K SF Estate on 40 Acres

10.0 out of 10, Exceptional, (31)
"We loved the Freeman estate for our wedding!! Daniel and Anna were super helpful and the property was amazing! The house had so many amenities it was beyond our expectations. Our guests were astounded by the home and the surrounding property, would HIGHLY recommend to anyone and everyone. "
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
HUGE KITCHEN 4 Private Acres, 7 Min to Town, WiFi, AC, Fireplace
Exterior

HUGE KITCHEN 4 Private Acres, 7 Min to Town, WiFi, AC, Fireplace

10.0 out of 10, Exceptional, (34)
"This house was adorably charming and perfect for a weekend getaway in Woodstock. We loved watching wildlife from the beautiful kitchen windows and the privacy the property provided. Our pup loved the front sun room and keeping an eye on the yard. Thank you for sharing your home!"
HUGE KITCHEN 4 Private Acres, 7 Min to Town, WiFi, AC, Fireplace
Lake Cottage, Private Beach, Kayaks, FirePit, Grill, 1 hour & 15 Minutes to NYC!
Beach nearby, beach towels

Lake Cottage, Private Beach, Kayaks, FirePit, Grill, 1 hour & 15 Minutes to NYC!

9.4 out of 10, Exceptional, (86)
"Perfectly adorable house that was ideal for our brief getaway. I wish we had been able to use the kayak/canoe but time was tight. The only issue was the driveway which had me holding my breath a bit but luckily we were careful and managed without incident."
Lake Cottage, Private Beach, Kayaks, FirePit, Grill, 1 hour & 15 Minutes to NYC!
High Point Mtn House ~ Celebrate Thanksgiving on the Mountain! Total privacy!
Terrace/patio

High Point Mtn House ~ Celebrate Thanksgiving on the Mountain! Total privacy!

10.0 out of 10, Exceptional, (21)
"My friends and I were looking for a place for 8 of us to enjoy the weekend and it was awesome. The house location has one of the most beautiful sights of any VRBO house I've stayed at. Between the incredible audio systems, furniture layout, overall living room aesthetics, and living room windows designed to take advantage of the beautiful view, the interior was ideal for our group. The host was in constant communication with us and gave clear directions for entering and leaving the house. Highly...
High Point Mtn House ~ Celebrate Thanksgiving on the Mountain! Total privacy!
The Studio at the Inn at High Falls
Exterior

The Studio at the Inn at High Falls

7.8 out of 10, Good, (22)
"Great communication with host. Stayed one night for event at Arrowood Farms (only 10 minutes away). Clean , nicely decorated studio with plenty of light. Lovely yard. Close to all local attractions and dining. Large shower. Great towels and toiletries.TV and A/C worked well. Appreciated the drinking water.Really cozy studio. Has frig, microwave and coffee maker.(also iron and hair dryer). A fabulous stay, although water pressure was a little low, but certainly not a deal breaker. Had people...
The Studio at the Inn at High Falls
Spectacular Short Term Vacation Rental in Kent
Exterior

Spectacular Short Term Vacation Rental in Kent

9.6 out of 10, Exceptional, (76)
"Hosts were great and very responsive and the property was fantastic and really peaceful. Highly recommend staying there!"
Spectacular Short Term Vacation Rental in Kent
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
Property grounds

Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream

9.2 out of 10, Wonderful, (39)
"2 nights in a delightful cottage. It is small but delightfully appointed. The highlight was this clean, warm little cottage is perched directly on swft stream. We left the backdoor open at night!"
The price is NZ$476
includes taxes & fees
24 Nov - 25 Nov
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
Hamptons on the Hudson in South Saugerties
Terrace/patio

Hamptons on the Hudson in South Saugerties

10.0 out of 10, Exceptional, (12)
"Our group of 7 women had a great time in the house. Beautiful property. Nice view of the Hudson. Lots of amenities. Well stocked kitchen. Cozy and comfortable. We enjoyed the Nespresso machine. Lots of room for us to spread out and to hang out together in the living room and enjoy a meal in the dining room. We would definitely stay again. "
Hamptons on the Hudson in South Saugerties
Charming Artist's Retreat
Exterior

Charming Artist's Retreat

9.8 out of 10, Exceptional, (129)
"Escaped Long Island’s noise, traffic and overall stress . Listened to owls, watched birds soaring, kicked up leaves and gazed at the periwinkle colored mountains while perched on a bench. Felt safe enough knowing civilization was near enough, would have liked a landline phone just in case of an emergency "
Charming Artist's Retreat
LOCATION! Location! Walking distance to Hunter MT! 3rd night 1/2 price w/weekend
Fridge, microwave, oven, stovetop

LOCATION! Location! Walking distance to Hunter MT! 3rd night 1/2 price w/weekend

9.6 out of 10, Exceptional, (45)
"We really enjoyed our stay in Hunter. The house met our needs well for a large family gathering. The hot tub and game room were excellent. Beutiful inside.It is close to shopping and hiking trails in the area. We did a lot of cooking and could have used larger cutting boards and baking/roasting pans. Be aware that the house is right on the main road into Hunter. The pinball machine was frustrating at times because the ball would get stuck.Overall it was a great stay."
LOCATION! Location! Walking distance to Hunter MT! 3rd night 1/2 price w/weekend
Sexiest Lil Cabin in Saugerties, NY
Exterior

Sexiest Lil Cabin in Saugerties, NY

8.6 out of 10, Excellent, (7)
"We loved our stay here, it was the perfect short getaway. Thanks Alexandria!"
Sexiest Lil Cabin in Saugerties, NY
Campfire Cottage: Fireplace, fire pit & no chores!
Fridge, microwave, oven, stovetop

Campfire Cottage: Fireplace, fire pit & no chores!

10.0 out of 10, Exceptional, (20)
"Fantastic stay in the campfire cottage! Every detail was taken care of, from extra toothpaste (I always forget mine!) to the Nespresso machine. Cottage was very clean and cozy, communication was excellent. Would definitely return!"
The price is NZ$312
includes taxes & fees
24 Nov - 25 Nov
Campfire Cottage: Fireplace, fire pit & no chores!
Private Estate, Heated YEARROUND Outdoor Pool
Fridge, microwave, oven, stovetop

Private Estate, Heated YEARROUND Outdoor Pool

10.0 out of 10, Exceptional, (13)
"The country setting provided a quiet retreat. The home is well equipped: plenty of beds, multiple gathering places, pool with towels (although it was pretty cold until the pool guy came and provided help). The outdoor grill provides additional cooking space. The home is within easy driving to many places of interest. We had a nice week at this home."
Private Estate, Heated YEARROUND Outdoor Pool
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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