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Dover Plains Vacation Rentals

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Check prices for these dates

In two weeks
Oct 31 - Nov 2
In two months
Dec 12 - Dec 14
In three months
Jan 9 - Jan 11
In four months
Feb 6 - Feb 8

Vacation Rentals in Dover Plains

Outdoor dining
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
9.6 out of 10, Exceptional, (39)
"Plenty of seating & comfortable beds were a plus! The theatre room was really fun for grandkids!"
The price is ￥39,453
￥51,007 total
includes taxes & fees
Nov 2 - Nov 3
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Terrace/patio
Log Cabin On A Lake With Private Dock & Beach! One Hour from NYC! No Pet Fees!
Log Cabin On A Lake With Private Dock & Beach! One Hour from NYC! No Pet Fees!
10.0 out of 10, Exceptional, (194)
"Wonderful place to rest and recharge."
Log Cabin On A Lake With Private Dock & Beach! One Hour from NYC! No Pet Fees!
Smart TV, fireplace
1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views
1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views
9.0 out of 10, Wonderful, (42)
"Perfect spot for a get together with friends... kitchen, dining room and living room all connected so you're always together and not missing out on the fun. Comfy couches and plenty of space for large board games."
1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views
Outdoor dining
Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed
Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed
9.4 out of 10, Exceptional, (30)
"Stayed here to visit family and it was perfect for what we needed. Would recommend staying here. "
Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed
Dining
Lakeside/Sleeps20/HotTub/GameRoom/2Acres/Firepit
Lakeside/Sleeps20/HotTub/GameRoom/2Acres/Firepit
10.0 out of 10, Exceptional, (2)
"This is a property that is very good for large family gatherings, which is how we gathered for a birthday celebration. This area of CT. is great and has lots to do.The house is in the perfect location to do all of it.Again, suits large groups well. Room for everyone."
Lakeside/Sleeps20/HotTub/GameRoom/2Acres/Firepit
Dining tables
Chestnut on Willow Lake
Chestnut on Willow Lake
9.4 out of 10, Exceptional, (3)
"We really enjoyed the privacy of the grounds, lake, dock , swimming, boats and paddle boards. The kitchen was well equipped and the beds were comfy. We had a great stay, thanks."
The price is ￥60,476
￥87,956 total
includes taxes & fees
Oct 15 - Oct 16
Chestnut on Willow Lake
Fridge, microwave, oven, stovetop
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
10.0 out of 10, Exceptional, (90)
"My family and I loved this property! We enjoyed walking around the woods and exploring. The house was well equipped and was really charming. We also loved sightseeing around the near by towns. Definitely a place to come back to stay again. "
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
Children's area
Hickory on Willow Lake
Hickory on Willow Lake
9.6 out of 10, Exceptional, (4)
"Cute cottage on nice grounds with a small lake. Kayaks and life jackets available for use was a big plus"
The price is ￥64,740
￥93,497 total
includes taxes & fees
Oct 15 - Oct 16
Hickory on Willow Lake
Exterior
Rustic Cabin in Fishkill!
Rustic Cabin in Fishkill!
10.0 out of 10, Exceptional, (2)
"The place was very nice, we met the owner and he was also bery accommodating. This is definitely a family friendly spot. "
The price is ￥34,471
￥54,588 total
includes taxes & fees
Nov 1 - Nov 2
Rustic Cabin in Fishkill!
Interior
Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
10.0 out of 10, Exceptional, (1)
"Great host"
The price is ￥48,624
￥120,111 total
includes taxes & fees
Oct 27 - Oct 28
Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
Cozy cabin with deck and fireplace steps from White Pond Lake. Dog friendly.
Cozy cabin with deck and fireplace steps from White Pond Lake. Dog friendly.
3.0 star property
10.0 out of 10, Exceptional, (2)
"It was great! We loved staying in this cute house. Proximity to the lake is great, and the backyard is quite beautiful."
Cozy cabin with deck and fireplace steps from White Pond Lake. Dog friendly.
Outdoor dining
The Goshen Glass Chalet
The Goshen Glass Chalet
9.6 out of 10, Exceptional, (40)
"The chalet was great. Plenty of room, very cozy and in a very quiet neighborhood community. "
The Goshen Glass Chalet
Exterior
Spacious 4BD Country Gem - Fire Pit & Chill Vibes
Spacious 4BD Country Gem - Fire Pit & Chill Vibes
10.0 out of 10, Exceptional, (11)
"We had a lovely weekend stay at this stone house with our family. There were a lot of lovely artistic touches throughout the house and it was obvious it was well cared for. The hosts have gone above and beyond making sure we had everything we needed. Kitchens and bathrooms were well stocked and lots of lovely "welcome" items in all the rooms. Would definitely recommend staying here again."
Spacious 4BD Country Gem - Fire Pit & Chill Vibes
Exterior
The Farm at Hyde Park
The Farm at Hyde Park
9.8 out of 10, Exceptional, (80)
"This was the perfect option for us for a nearby wedding. We ate twice at the River & Post (excellent) and went into Rhinebeck for the Sunday market. The property itself was very accommodating and had everything we needed. The kitchen was well equipped, beds comfortable, and plenty of seating options in the main room. The outside area was also a perfect place for coffee in the morning and we loved the chickens running around. Glenn could not have been nicer. Highly recommend!"
The Farm at Hyde Park
Smart TV, fireplace, books
Private Beautiful Home - Family Friendly - 1 min. Walk to Candlewood Lake
Private Beautiful Home - Family Friendly - 1 min. Walk to Candlewood Lake
10.0 out of 10, Exceptional, (13)
"The house worked very well for our family holiday. Very clean, had everything we needed "
The price is ￥31,989
￥80,354 total
includes taxes & fees
Oct 15 - Oct 16
Private Beautiful Home - Family Friendly - 1 min. Walk to Candlewood Lake
Exterior
Summer Lake Cottage, private beach, Berkshire Hills, small village
Summer Lake Cottage, private beach, Berkshire Hills, small village
9.4 out of 10, Exceptional, (83)
"The house has rustic charm and sits right on the lake. It is a beautiful peaceful spot. "
Summer Lake Cottage, private beach, Berkshire Hills, small village
Terrace/patio
Spacious New Luxurious holiday house in lovely Hudson Valley
Spacious New Luxurious holiday house in lovely Hudson Valley
9.8 out of 10, Exceptional, (19)
"We loved our stay at this gorgeous home & we will definitely book it again in the future!"
The price is ￥57,830
￥106,134 total
includes taxes & fees
Oct 27 - Oct 28
Spacious New Luxurious holiday house in lovely Hudson Valley
Interior
Lakefront Fall Foliage in New England Just 2 Hours From NYC
Lakefront Fall Foliage in New England Just 2 Hours From NYC
10.0 out of 10, Exceptional, (84)
"Great location and fully equipped cabin! I hope to return sometime soon Everything was perfect!"
Lakefront Fall Foliage in New England Just 2 Hours From NYC
1 bedroom, WiFi, bed sheets
Charming 1-bedroom apartment in Carmel with WiFi, AC
Charming 1-bedroom apartment in Carmel with WiFi, AC
10.0 out of 10, Exceptional, (1)
"Didn’t expect the layout separate entrance. Very clean and great amenities. Highly recommended and very nice family. "
The price is ￥16,027
￥36,520 total
includes taxes & fees
Oct 15 - Oct 16
Charming 1-bedroom apartment in Carmel with WiFi, AC
Fridge, microwave, oven, stovetop
NEW! Gated 21 Acre Modern Luxury Estate Heated Pool Hot Tub Gym Movie Theater.
NEW! Gated 21 Acre Modern Luxury Estate Heated Pool Hot Tub Gym Movie Theater.
9.6 out of 10, Exceptional, (56)
"We hosted a get-away weekend with friends and the property was perfect. There was lots of privacy, which was nice. The home was well stocked. Communications with the property host and property manager was easy. Everything at the home was in working condition. We had a great time."
NEW! Gated 21 Acre Modern Luxury Estate Heated Pool Hot Tub Gym Movie Theater.
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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Top Dover Plains Hotel Reviews

HYATT house Fishkill/Poughkeepsie

HYATT house Fishkill/Poughkeepsie

10/10 Excellent
"The location was in the middle of 3 places I visited! I loved that Walmart was across the street! My friend got sick and I went there several times. The staff was very friendly. "
Elsie 7-night trip
Posted 16 hours ago
HYATT house Fishkill/Poughkeepsie

Find out more about Dover Plains

Search for holiday rentals in Dover Plains on Expedia! You can easily find your home rentals, villas, holiday apartments in Dover Plains using one of the methods below:

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Look no further and take a look at our great range of rental properties in Dover Plains!

Frequently asked questions

Are there vacation rentals in Dover Plains?

Yes, we give you a choice of vacation rentals close to well known local attractions in Dover Plains, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best vacation rentals that Dover Plains has to offer?

Privacy in the hills one hour from NYC and minutes to Breakneck Mtn. : This vacation home rental near Dover Plains is located in the mountains and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the garden in this rental home to help you unwind.

How many vacation rentals are there in Dover Plains?

Choose from 4 Expedia vacation rentals in Dover Plains for a memorable vacation.

What’s there to see and do in Dover Plains?

While exploring the area, visit family-friendly sights like Mid-Hudson Civic Center, or get outside and enjoy nature at Dover Plains Stone Church. Dover Town Hall and Orvis Sandanona Shooting Grounds are a couple of places you'll find in the larger area.

What’s a vacation rental in Dover Plains like?

A vacation rental is a private property you can book for short or long periods in Dover Plains. Vacation rentals offer amenities such as laundry facilities and kitchens so you'll feel just like you're at home. If you're concerned about a clean environment, a vacation rental can offer a sense of safety away from public hotel elevators and busy lobbies while still allowing you to travel. You'll also get more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is an attractive choice for families.