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Search Holiday Rentals in Dover Plains

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Check prices for these dates

Tonight
9 Oct - 10 Oct
Tomorrow
10 Oct - 11 Oct
This weekend
10 Oct - 12 Oct
Next weekend
17 Oct - 19 Oct

Top Holiday Rentals in Dover Plains

Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
Fridge, microwave, oven, stovetop

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.
Log Cabin On A Lake With Private Dock & Beach! One Hour from NYC! No Pet Fees!
Terrace/patio

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!
The House In Highland- Secluded Retreat
Outdoor dining

The House In Highland- Secluded Retreat

10.0 out of 10, Exceptional, (14)
"Very nice location and private."
The House In Highland- Secluded Retreat
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Outdoor dining

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 CHF 269
includes taxes & fees
2 Nov - 3 Nov
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Chestnut on Willow Lake
Exterior

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 CHF 470
includes taxes & fees
13 Oct - 14 Oct
Chestnut on Willow Lake
Lakefront Fall Foliage in New England Just 2 Hours From NYC
Interior

Lakefront Fall Foliage in New England Just 2 Hours From NYC

10.0 out of 10, Exceptional, (83)
"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
Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed
Outdoor dining

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
Lakeside/Sleeps20/HotTub/GameRoom/2Acres/Firepit
Dining

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
Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
Interior

Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY

The price is CHF 592
includes taxes & fees
11 Oct - 12 Oct
Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
The Farm at Hyde Park
Exterior

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
Rustic Cabin in Fishkill!
Exterior

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 CHF 289
includes taxes & fees
1 Nov - 2 Nov
Rustic Cabin in Fishkill!
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.
1 Br Private Victorian Apt in Convenient City Location on Half Acre Sleeps 4
Apartment, 1 Bedroom, Balcony, Garden View | Living area

1 Br Private Victorian Apt in Convenient City Location on Half Acre Sleeps 4

2.0 star property
9.0 out of 10, Wonderful, (8)
"Gary is a great host and provides a wonderful experience. He is the best and it was a very nice stay. Best host I have had before."
The price is CHF 164
includes taxes & fees
13 Oct - 14 Oct
1 Br Private Victorian Apt in Convenient City Location on Half Acre Sleeps 4
Candlewood Lake Retreat; Dock, Game Room & Firepit
Outdoor dining

Candlewood Lake Retreat; Dock, Game Room & Firepit

10.0 out of 10, Exceptional, (47)
"Everything was great! Thank you!"
The price is CHF 1'178
includes taxes & fees
13 Oct - 14 Oct
Candlewood Lake Retreat; Dock, Game Room & Firepit
Be in Nature at this Gorgeous Riverfront Cabin
Smart TV, books

Be in Nature at this Gorgeous Riverfront Cabin

10.0 out of 10, Exceptional, (21)
"An ideal retreat. The modern cabin offered serene surroundings with stunning views of the woods and creek. The property was well-maintained, and the property manager was highly responsive. A perfect choice for a peaceful and refreshing getaway."
Be in Nature at this Gorgeous Riverfront Cabin
Summer Lake Cottage, private beach, Berkshire Hills, small village
Exterior

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
Spacious 4BD Country Gem - Fire Pit & Chill Vibes
Exterior

Spacious 4BD Country Gem - Fire Pit & Chill Vibes

9.8 out of 10, Exceptional, (10)
"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
The Goshen Glass Chalet
Outdoor dining

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
Charming 2-bedroom apartment waterfront with WiFi, lovely New Milford
TV, fireplace

Charming 2-bedroom apartment waterfront with WiFi, lovely New Milford

10.0 out of 10, Exceptional, (6)
"We were in town for a family wedding and found this quaint little apartment that was quiet and secluded. Being on the river we did find a lot of bugs, but nothing we couldnt handle. The owners were extremely nice and responsive and we had a wonderful stay. "
Charming 2-bedroom apartment waterfront with WiFi, lovely New Milford
NEW! Gated 21 Acre Modern Luxury Estate Heated Pool Hot Tub Gym Movie Theater.
Fridge, microwave, oven, stovetop

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

SureStay Plus Hotel by Best Western Highland Poughkeepsie

SureStay Plus Hotel by Best Western Highland Poughkeepsie

10/10 Excellent
"Pets welcome "
Woo 1-night trip
Posted 2 days ago
SureStay Plus Hotel by Best Western Highland Poughkeepsie

Frequently asked questions

Are there holiday rentals in Dover Plains?

Yes, there are holiday rentals close to the most popular sights in Dover Plains, or you can select a more secluded option if you're looking for a relaxing stay.

How many holiday rentals are there in Dover Plains?

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

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 wider area.

What’s a holiday rental in Dover Plains like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Dover Plains. Holiday rentals feature amenities such as patios, hot tubs and fire pits so your stay will be comfortable. If you're concerned about a sanitised environment, a holiday rental can offer a sense of privacy away from public hotel lifts and bustling concierge desks while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive option for family trips.