Search Chichester Cottage Rentals from CA $219

    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
Aug 15 - Aug 17
In two weeks
Aug 22 - Aug 24
In one month
Sep 5 - Sep 7
In two months
Oct 3 - Oct 5

Browse Select Chichester Cottages

Streamside Cottage Half Mile to Town of Woodstock
Exterior

Streamside Cottage Half Mile to Town of Woodstock

10.0 out of 10, Exceptional, (246)
"A beautiful quiet setting! "
The price is CA $219
CA $464 total
includes taxes & fees
Sep 2 - Sep 3
Streamside Cottage Half Mile to Town of Woodstock
Junebug Cottage: peace, love and privacy a short walk to Woodstock village green
Set amidst a serene wooded area, this two-story house offers a retreat with a well-manicured lawn and a small deck.

Junebug Cottage: peace, love and privacy a short walk to Woodstock village green

10.0 out of 10, Exceptional, (71)
"We were in Woodstock for a wedding. Junebug Cottage was perfect for our stay! "
Junebug Cottage: peace, love and privacy a short walk to Woodstock village green
Romantic cottage with hot tub . Close to hiking and breweries . Pet friendly!
Experience the charm of Pinewood Inn, featuring a covered porch and a cozy gazebo.

Romantic cottage with hot tub . Close to hiking and breweries . Pet friendly!

9.8 out of 10, Exceptional, (18)
"Had a wonderful "
Romantic cottage with hot tub . Close to hiking and breweries . Pet friendly!
Leggett Cottage, High Falls, NY.
Stylish single-story home with a gabled roof and inviting front porch.

Leggett Cottage, High Falls, NY.

10.0 out of 10, Exceptional, (76)
"We really enjoyed our stay! The space was very nice & beautiful during the fall!"
Leggett Cottage, High Falls, NY.
Cedar Cottage with hot tub as seen in New York Times escape section.
Cozy cabin nestled in a dense forest, offering a serene retreat with a central window and small porch area.

Cedar Cottage with hot tub as seen in New York Times escape section.

9.4 out of 10, Exceptional, (84)
"Diana’s property was the perfect spot to reconnect with old friends. We enjoyed the art, food and music of Woodstock and a side trip to Bethel to check out the Woodstock Museum. Diana’s home was a comfortable place to retreat to after our days of exploring. We would love to make it an annual event. "
Cedar Cottage with hot tub as seen in New York Times escape section.
NEW! Herb Cottage: Historic Artist's Cottage, Wood Stove, Walk to Town!
Traditional architecture meets serene gardens in this charming two-story building with a welcoming porch.

NEW! Herb Cottage: Historic Artist's Cottage, Wood Stove, Walk to Town!

9.8 out of 10, Exceptional, (134)
"We had a marvelous visit!"
NEW! Herb Cottage: Historic Artist's Cottage, Wood Stove, Walk to Town!
Private Home ~ All Yours ~ In town ~ fenced in yard ~ Hot Tub ~ Pets welcome!
Set amidst a tranquil forest, this charming home features a two-story facade with a welcoming yellow door and a picket fence.

Private Home ~ All Yours ~ In town ~ fenced in yard ~ Hot Tub ~ Pets welcome!

9.8 out of 10, Exceptional, (116)
"The location was exceptional, close to restaurants and shops, quiet neighborhood, comfortable bed and the house was well stocked with everything you’d need."
The price is CA $530
CA $995 total
includes taxes & fees
Aug 23 - Aug 24
Private Home ~ All Yours ~ In town ~ fenced in yard ~ Hot Tub ~ Pets welcome!
The Cabin at Chichester in the Catskills Mountains
Situated in a serene landscape, this charming home offers a peaceful retreat.

The Cabin at Chichester in the Catskills Mountains

9.8 out of 10, Exceptional, (185)
"This is a great little cottage! It’s super clean and has everything you need and plenty of space inside and out. Host was terrific to deal with and made the process seamless and simple. Would definitely stay here again as a great place to stay while enjoying all the area has to offer!! "
The Cabin at Chichester in the Catskills Mountains
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
Enjoy a peaceful retreat with a view of the lush forest from this outdoor deck, featuring a table, chairs, and potted plants.

Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream

9.0 out of 10, Wonderful, (42)
"This is a great place to stay. Really loved the fire pit by the creek for evening cocktails and conversation."
The price is CA $247
CA $423 total
includes taxes & fees
Aug 24 - Aug 25
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
Charming Artist's Retreat
Exterior

Charming Artist's Retreat

9.8 out of 10, Exceptional, (140)
"Enjoyed our stay!"
Charming Artist's Retreat
Private Woodstock cottage. Don't forget your dog!
Relax in this stylish room with a large bed, sofa, and dining table, perfect for unwinding and enjoying your stay.

Private Woodstock cottage. Don't forget your dog!

10.0 out of 10, Exceptional, (9)
"The property was Great! It was close to town, but far enough away for a little peace and quiet. The place itself was very clean, comfortable, and great for a couples weekend retreat."
Private Woodstock cottage. Don't forget your dog!
Catskills Cottage w/ Deck, 7 Mi to Hunter Mtn
Enjoy al fresco dining on the deck with a barbecue grill and comfortable seating.

Catskills Cottage w/ Deck, 7 Mi to Hunter Mtn

9.6 out of 10, Exceptional, (17)
"We loved the stay at this cabin."
Catskills Cottage w/ Deck, 7 Mi to Hunter Mtn
TOP RATED Romantic rustic luxury + flowing stream + walk to town = Brook Cottage
Enjoy outdoor dining or relaxation on the upper-floor balcony overlooking a beautifully maintained garden.

TOP RATED Romantic rustic luxury + flowing stream + walk to town = Brook Cottage

10.0 out of 10, Exceptional, (166)
"The hosts had thought of everything to make our stay comfortable - lovely bright rooms, well stocked kitchen, plush linens and towels, within walking distance of all restaurants and shops and a beautiful stream and lawn outside! Excellent!"
TOP RATED Romantic rustic luxury + flowing stream + walk to town = Brook Cottage
Charming 2-bedroom cottage with large deck in beautiful Accord NY.
Situated on a gently sloping hill, this house offers a scenic view of the surrounding forest from its wooden deck and stone pathway.

Charming 2-bedroom cottage with large deck in beautiful Accord NY.

10.0 out of 10, Exceptional, (13)
"It was better than the pictures! Very peaceful and a lovely little house. Judy was very responsive with any questions or needs we had. "
Charming 2-bedroom cottage with large deck in beautiful Accord NY.
ADORABLE CREEK COTTAGE Charming Original Details, Fireplace, Near Town, WiFi
Escape to a secluded cabin surrounded by tall trees and a gravel path, offering a peaceful retreat.

ADORABLE CREEK COTTAGE Charming Original Details, Fireplace, Near Town, WiFi

10.0 out of 10, Exceptional, (80)
"This was just what we were looking for. The host was very quick to respond to any of my questions. We enjoyed the location and all the amenities. The outdoor grill, outdoor firepit and inside fireplace were enjoyed and it was a nice bonus that there was plenty of firewood."
ADORABLE CREEK COTTAGE Charming Original Details, Fireplace, Near Town, WiFi
TOP-RATED! Pristine style+romantic luxury+firepit+walk to town=Brook Cottage Too
Situated on a corner of Old Forge Rd. and Mill Hill Rd., this traditional building offers a charming garden setting.

TOP-RATED! Pristine style+romantic luxury+firepit+walk to town=Brook Cottage Too

10.0 out of 10, Exceptional, (119)
"The property was lovely, and the perfect location. Chelsea was great to work with!"
TOP-RATED! Pristine style+romantic luxury+firepit+walk to town=Brook Cottage Too
Mountain Views & Brook Access: Home in Arkville!
House (3 Bedrooms) | Interior

Mountain Views & Brook Access: Home in Arkville!

3.0 star property
Mountain Views & Brook Access: Home in Arkville!
THE HIDDEN COTTAGE Private, Relaxing, Great Location, Has Everything You Need
Cozy cabin with a central double door and two smaller windows, set amidst a serene natural landscape.

THE HIDDEN COTTAGE Private, Relaxing, Great Location, Has Everything You Need

9.0 out of 10, Wonderful, (8)
"We really enjoyed our stay and will definitely come back. Highly recommended!"
THE HIDDEN COTTAGE Private, Relaxing, Great Location, Has Everything You Need
Cabin 4 Mi to Belleayre Mountain: Ski, Hike & Fish
Enjoy the serene views from the spacious deck, featuring a covered patio with Adirondack chairs and a wooden railing.

Cabin 4 Mi to Belleayre Mountain: Ski, Hike & Fish

3.0 star property
10.0 out of 10, Exceptional, (1)
"We had a great time during our stay. The house was nicely setup. We would go back again."
Cabin 4 Mi to Belleayre Mountain: Ski, Hike & Fish
2 Person Rain Shower-Cozy Cottage+King Bed+15 Min ⛷️Kayaks+Wine Barrel Table
Set amidst a serene forest, this single-story house offers a secluded retreat.

2 Person Rain Shower-Cozy Cottage+King Bed+15 Min ⛷️Kayaks+Wine Barrel Table

10.0 out of 10, Exceptional, (4)
"A great place to stay for Belleayre for a small family or two couples. Shower is great and TVs in all rooms is a plus with Netflix and good Wi-Fi. Close to Margaretville town center and kitchen is pretty well stocked and clean. I would stay there again."
2 Person Rain Shower-Cozy Cottage+King Bed+15 Min ⛷️Kayaks+Wine Barrel Table
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

Top Chichester Hotel Reviews

Best Western Plus Kingston Hotel And Conference Center

Best Western Plus Kingston Hotel And Conference Center

10/10 Excellent
"It was very conveniently located, walkable to the downtown historic areas of town, shopping and restaurants "
Grazyna 1-night trip
Posted 1 day ago
Best Western Plus Kingston Hotel And Conference Center