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Vacation rentals in Dover

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Top-rated vacation rentals in Dover

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

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Cabin in Pawling

4.95 out of 5 average rating, 110 reviews

Serene, Peaceful Cabin by the Lake

Take a stroll down to the lake in the crisp morning air, then light the fire and sink into the cherry leather armchair at this rustic log cabin. Touches of soft sage add a soothing side, while patterned rugs and chunky beams keep things homey. Authentic Log cabin, private lake with swimming, kayaking --1000's acres adjacent private land, fishing, hunting-- Enjoy the harvest of the Hudson Valley-- minutes to wineries, Pawling train to NYC, Appalachian trail and hiking, Child safe. Minutes walk to Lake! Private Lake-- We are here to check you in and only if you need us. We respect your privacy and "time-away". The property sits in a private, sprawling lake community minutes from wineries for tastings, Pawling station for trains to New York City, and the Appalachian trail for scenic hiking. Explore Wallkill and Warwick within around an hour's drive. Car, Metro North (train to NYC), Uber, Lyft...

Dec 23 – 30

ﺩ.ﺇ858 per night

Apartment in Kent

4.93 out of 5 average rating, 127 reviews

Loft 22

Apartment/loft located above the garage in a private home. Set in the rolling hills of Kent, this 2 bedroom loft is cozy enough for anyone looking to explore this quaint little town. Sleeps 3 comfortably. Centrally located to all three private schools. 11 minute drive to Harlem Valley/Wingdale (NY) train station. *Pool is not solely for the use of the Air BNB. *Dogs on property. All friendly. *IF STAYING IN WINTER MONTHS. You must have 4 Wheel drive vehicle. Driveway/Road is long dirt road.*

Dec 6 – 13

ﺩ.ﺇ571 per night

Home in Danbury

4.99 out of 5 average rating, 336 reviews

BEAUTIFUL PRIVATE APARTMENT SUITE IN DANBURY CT!!

Private 1100 sq. Ft. suite staycation located in a beautiful, safe, quiet neighborhood in DanburyModern Kitchen, One Bathroom, One Luxury Queen Size Bed, 55” Smart TV with Cable/Amazon Prime/Netflix, Apple Cable charger next to bed, Wi-Fi, AC, Heat, Refrigerator, Countertop Oven, Microwave, Electric Hot Plate, Keurig Coffee Maker, Hair Dryer, Iron, Ironing Board, Shampoo, Conditioner, Body Wash. The space is nonsmoking inside and outside the premises including vaping. No children or infants

Sep 4 – 11

ﺩ.ﺇ580 per night

Guest suite in Lagrangeville

4.84 out of 5 average rating, 127 reviews

Renovated 1840 Collins Estate Private East Wing

The 1840 Collins Estate took 60 men three full years to construct. The rental is a private, locked East Wing of the home. Fully refinished with modern comforts; bedding, mattresses, bathrooms, coffee bar and more. The home is centrally located near the Links at Union Vale(1 mile), Millbrook, Rhinebeck, Beacon, Poughkeepsie and colleges. Historic sites and festivals abound. Many great restaurants nearby due to proximity to Culinary. Perfect hotel efficiency style getaway cared for with pride.

Aug 1 – 8

ﺩ.ﺇ531 per night

Guest suite in Bethlehem

4.99 out of 5 average rating, 200 reviews

Breezy Crest private & restful w/antique charm

Escape to this charming and historic two-story 1841 suite, nestled in the quaint town of Bethlehem. The upstairs bedroom boasts original exposed beams and antique details, creating a cozy and inviting atmosphere. Wake up to the sunrise from the comfort of your bed and enjoy a warm fire in the backyard while listening to the peaceful sounds of nature. Conveniently located between Litchfield and Woodbury, and just 90 miles from NYC, you'll have easy access to shops, restaurants, and ski slopes.

Sep 6 – 13

ﺩ.ﺇ606 per night

Guest suite in Sherman

4.98 out of 5 average rating, 134 reviews

Cozy Scenic New England country retreat w/ hiking

Cozy and private studio in attached guest house on 3 bucolic acres w/pond. Two free kayaks parked by the lake town beach (only 3 miles away). Self check-in with private entrance. Enjoy scenic views of pond and farms from deck & patio with your own grill & fire pit. Mosey or bike (2 bikes provided) along our scenic road to nature preserve. 3 miles to quaint town with restaurants & coffee. Close to Appalachian trail & other great hiking. Pets welcome. Inquire about min stay requirements.

Apr 21 – 26

ﺩ.ﺇ531 per night

Cabin in New Milford

4.95 out of 5 average rating, 146 reviews

The Cottage on Babbling Brook

Cozy, rustic cottage. Beautifully overlooking Wimsink Brook, with custom designed & handcrafted woodwork throughout the home. An all around great spot for families and friends. A magical, peaceful and relaxing space. Conveniently located on the Connecticut/New York border, just a 1 ½ hour drive or metro north from NYC. The area is a prime location, as it offers some of the most stunning and scenic hikes & drives in the country. Only a 10 minute drive from Kent, New Milford or Pawling.

Nov 29 – Dec 6

ﺩ.ﺇ871 per night

Guest suite in Dover Plains

4.91 out of 5 average rating, 262 reviews

Hoppy Hill Farm House

Enjoy the simple country life in this historic farmhouse. Watch the sun rise over the breathtaking mountain views from the front porch while sipping a cup of coffee/tea. For the more adventurous, there are lots of Appalachian Trail hiking opportunities, and nature preserves to enjoy. Thunder Ridge ski mountain and Daryl Hall’s bar only 15 mins away. Take a ride to near-by towns (Kent, Millbrook, Amenia, Wassaic) for great food, coffee shops, antiques, parks, breweries and vineries.

Jul 9 – 16

ﺩ.ﺇ545 per night

Home in Pawling

4.9 out of 5 average rating, 273 reviews

Appalachian Trail House! Easy access to NYC trains

Hike the Appalachian Trail! This is a cozy 3 bedroom, 1 bath, full basement and 3 acres of land. Located in town of Pawling, NY, about 90 minutes from NYC. Walking distance from Appalachian Trail train stop. Enjoy mother nature at it's finest with a short hike up historic Quaker Hill section of the Appalachian Trail. We accept up to 2 well behaved pets under 40 lbs. There is a $50 fee per pet. For companion and service dogs/pets, paperwork must be submitted before stay.

Nov 27 – Dec 4

ﺩ.ﺇ729 per night

Apartment in Brookfield

4.94 out of 5 average rating, 184 reviews

Peaceful apartment on 3.5 acres w/ Artist studio.

Welcome to our cozy apartment! This fully enclosed apartment is attached to our main house on a beautiful 3.5-acre property in Brookfield. Enjoy a kitchen, comfortable living and bedroom area, and a clean bathroom. Guests have access to a shared 32 ft, 10 ft deep pool, artist studio, pool table,, garden, fire space, and outdoor seating. We provide a guidebook for your convenience. Book now and experience a perfect blend of comfort, creativity, and relaxation.

Sep 13 – 20

ﺩ.ﺇ424 per night

Apartment in Stanfordville

4.95 out of 5 average rating, 152 reviews

Country Apartment great for a romantic getaway

Second story apartment above garage with private entrance has everything you need for a comfortable getaway. Located on quiet rural neighborhood road with off street parking. Enjoy nature right out your door walking to the beaver pond in the back woods or on the many nearby hiking and biking trails. Relax in the backyard. An easy drive from the Taconic Parkway or 20 minutes from the Metro-North Wassiac train station.

Jun 25 – Jul 2

ﺩ.ﺇ503 per night

Apartment in Millbrook

4.93 out of 5 average rating, 205 reviews

Red Tail Ridge

One BR with bath, full kitchen, eating area and living room. Separate entrance and sliding glass door in rear with country views. Located on 12 acre parcel. Close to village of Millbrook (less than 4 miles). We are located in center of Dutchess County. There is great antique shopping, historic sites and some of the finest restaurants and chefs with tastes to suit most everyone. .

Aug 7 – 14

ﺩ.ﺇ474 per night

Vacation rentals for every style

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Hotels

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Homes

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Popular amenities for Dover vacation rentals

Free parking on premises

Air conditioning

Stay near Dover's top sights

Dover Stone Church31 locals recommend

Big W's Roadside Bar B Que13 locals recommend

Kelly’s Creamery & Kelly's Husband's Truck12 locals recommend

Stone Church12 locals recommend

Old Drovers Inn5 locals recommend

Crown Maple Estate4 locals recommend

Other great vacation rentals in Dover

Guesthouse in New Milford

4.94 out of 5 average rating, 177 reviews

Charming Cottage w/Pastoral Views

Mar 8 – 15

ﺩ.ﺇ609 per night

Cottage in Kent

4.88 out of 5 average rating, 149 reviews

NEW - Hot Tub - Mohawk Mtn - Appalachian Trl

Dec 13 – 20

ﺩ.ﺇ1,139 per night

Guest suite in Kent

5.0 out of 5 average rating, 56 reviews

Bright 1-bedroom in walking distance to town

Mar 19 – 26

ﺩ.ﺇ457 per night

Home in Dover Plains

4.91 out of 5 average rating, 34 reviews

5 Harts Rd - Newly built home in Dover, NY

Aug 14 – 21

ﺩ.ﺇ507 per night

Apartment in Amenia

5.0 out of 5 average rating, 22 reviews

Amenia Main St Cozy Studio

Aug 22 – 29

ﺩ.ﺇ282 per night

Guesthouse in Sharon

5.0 out of 5 average rating, 65 reviews

Cottage with a Waterfall View

Sep 26 – Oct 3

ﺩ.ﺇ400 per night

Cottage in Pawling

5.0 out of 5 average rating, 61 reviews

Twin Lakes Designer A-frame Stone Cottage

Dec 9 – 16

ﺩ.ﺇ1,328 per night

Home in Dover Plains

5.0 out of 5 average rating, 11 reviews

Blue Heron - Scenic Oasis on Working Farm

Sep 22 – 29

ﺩ.ﺇ1,108 per night

Destinations to explore