Search Guest Houses in Pine Plains

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
18 Jul - 20 Jul
In two weeks
25 Jul - 27 Jul
In one month
8 Aug - 10 Aug
In two months
5 Sep - 7 Sep

Guest Houses in Pine Plains

The Wiltwyck
Superior Suite | Living area | 32-inch Smart TV with digital channels, TV, Netflix

The Wiltwyck

3.5 star property
9.6 out of 10, Exceptional, (148)
"Very nice property charming "
The Wiltwyck
The Gables of Rhinebeck Inn
Property entrance

The Gables of Rhinebeck Inn

3.0 star property
9.2 out of 10, Wonderful, (105)
"Large clean room. Comfy beds. Great location. Lovely stay!!"
The Gables of Rhinebeck Inn
Private one bedroom guesthouse with pool
Fridge, microwave, oven, stovetop

Private one bedroom guesthouse with pool

9.8 out of 10, Exceptional, (38)
"Sharon and John are so on top of things. I forgot my stuff there and they arranged to have my things picked up and returned to me, thank you "
Private one bedroom guesthouse with pool
Tivoli Star Gazing Cabin - External 2
Terrace/patio

Tivoli Star Gazing Cabin - External 2

The price is SAR 41,680
SAR 51,913 total
includes taxes & fees
14 Jul - 15 Jul
Tivoli Star Gazing Cabin - External 2
Hudson valley and The Berkshires Cottage
Exterior

Hudson valley and The Berkshires Cottage

10.0 out of 10, Exceptional, (9)
"A great stay in this well situated getaway. The owners were helpful and communicative, and the house was easy driving distance to Great Barrington, Hillsdale and Lenox. The unit is open and airy and decorated in a very pet friendly way. Would stay again without hesitation."
The price is SAR 323
SAR 1,162 total
includes taxes & fees
22 Jul - 23 Jul
Hudson valley and The Berkshires Cottage
9 Academy
The Parlor Suite | 1 bedroom, Egyptian cotton sheets, premium bedding, pillowtop beds

9 Academy

4.0 star property
9.6 out of 10, Exceptional, (5)
"The Loft was so beautifully decorated and every detail was perfect. "
The price is SAR 2,110
SAR 2,426 total
includes taxes & fees
13 Jul - 14 Jul
9 Academy
LEEDS A GREAT ESCAPE
Property grounds

LEEDS A GREAT ESCAPE

9.0 out of 10, Wonderful, (36)
"Peaceful and quiet but not too far away from some great restaurants and beautiful views!"
LEEDS A GREAT ESCAPE
Hits | Catskills Views | Pet Friendly | Studio
Exterior

Hits | Catskills Views | Pet Friendly | Studio

10.0 out of 10, Exceptional, (1)
"Great property just down the road from HITS. It was as described and very comfortable. We would stay here again. "
The price is SAR 634
SAR 1,206 total
includes taxes & fees
3 Aug - 4 Aug
Hits | Catskills Views | Pet Friendly | Studio
Bowie Mountain Studio in heart of the Hudson-Valley's best nature, food, shops.
Exterior

Bowie Mountain Studio in heart of the Hudson-Valley's best nature, food, shops.

10.0 out of 10, Exceptional, (25)
"Really enjoyed the stay here - very easy and communication was great. Would stay again and recommend highly!"
Bowie Mountain Studio in heart of the Hudson-Valley's best nature, food, shops.
The Woodbine Inn
BBQ/picnic area

The Woodbine Inn

3.5 star property
9.6 out of 10, Exceptional, (17)
"Beautiful, clean, amazing staff and supe cozy"
The Woodbine Inn
Renovated Private Guest House by Evergreen Home
Outdoor dining

Renovated Private Guest House by Evergreen Home

10.0 out of 10, Exceptional, (9)
"Great stay. Cute spot!"
Renovated Private Guest House by Evergreen Home
1805 House Bed and Breakfast
Exterior

1805 House Bed and Breakfast

3.0 star property
9.8 out of 10, Exceptional, (38)
"Very nice stay. Perhaps a little over priced considering lack of amenities and an average breakfast."
1805 House Bed and Breakfast
Church Des Artistes Guest House
Building design

Church Des Artistes Guest House

3.0 star property
9.4 out of 10, Exceptional, (18)
"This was a very overpriced bed and breakfast! The owners were quite pleasant, but there were several things about this establishment that raised a flag. For one, we had to go down the hall and down a full flight of stairs to the bathroom. At the bottom of the stairs (where our "private bathroom" was) was also the door to the entrance of the house. Althugh there was not much traffic, it was still rather uncomfortable to walk up the stairs with my towel on! Our beds were never made on...
Church Des Artistes Guest House
Bohemian Inn
Property grounds

Bohemian Inn

2.5 star property
7.8 out of 10, Good, (35)
"My husband summed up our overnight stay. He said, "I feel like we just had a mini vacation!" The Bohemian Inn is in such a convenient location. You can walk to to most anything you might want/need. Stephanie, the owner/operator of the Inn was wonderful! She made our stay feel as though we were visiting an old friend, while maintaining privacy. The rooms are lovely. They are beautifully and uniquely decorated. And spotlessly clean!! A mini, wonderful vacation, indeed! Working in...
Bohemian Inn
Vanderbilt Lakeside
Standard Room, 1 Queen Bed, Partial Lake View | Egyptian cotton sheets, premium bedding, individually decorated

Vanderbilt Lakeside

3.5 star property
9.4 out of 10, Exceptional, (26)
"We loved our stay at the Vanderbilt Lakeside! The house is so stylish and we had a wonderful dinner at the restaurant. Would definitely stay again!"
Vanderbilt Lakeside
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free