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Cottage holiday rentals in Woodstock

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Top-rated cottage rentals in Woodstock

Guests agree: These cottages are highly rated for location, cleanliness and more.

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Cottage in Phoenicia

4.91 out of 5 average rating, 577 reviews

Romantic Getaway in Lovingly Restored Esopus Cottage

This cottage is perfect for relaxation, working remotely and as a hub for experiencing the majestic Catskills. Featured in Curbed NY, a travel magazine, as “The Best Vacation Rentals in the Hudson Valley," the Esopus Cottage has over 1500 five-star reviews. (Inquire regarding 1-night stays from Sunday to Thursday at a special rate!) As Superhosts for 10+ years, we are committed to stellar customer service and making your vacation a memorable and restorative experience. License # 2023-STR-055P

18 – 25 July

$1,700 AUD total

Guest favourite

Cottage in Highland

4.91 out of 5 average rating, 538 reviews

Little Yellow Cottage New Paltz - Kitchen wash/dry

Built over 100 years ago as a chicken hatchery, this gorgeous little gem has been fully restored as a two-story guest cottage. Located in New Paltz just minutes off Exit 18 on I-87 in a very private, quiet, country setting. Only ten minutes from New Paltz Village & SUNY New Paltz and set back on a lightly traveled road for those long summer strolls. You don't even need a car to get here! It's just 12 minutes by taxi from the New Paltz Bus Station or bring your bike up and cycle everywhere!

15 – 22 Sept

$1,807 AUD total

Guest favourite

Cottage in Accord

4.88 out of 5 average rating, 216 reviews

Sweet Cottage on a Farm Road

Simple, airy, studio cottage next to my house, featuring a woodstove & enormous bathroom with a clawfoot tub. Perfect for writers/solo-travelers seeking solitude & peace and couples wanting quality time together. The cottage is on a scenic country road, walking distance to 3 farms, including 2 great farm-to-table restaurants: Westwind Pizza/Apple Orchard, Arrowood Brewery, & Hollengold Farm. A stone's throw are Stonehill Barn and Inness. 15 min drive to the incomparable Minnewaska State Park.

9 – 16 May

$1,020 AUD total

Guest favourite

Cottage in Saugerties

4.93 out of 5 average rating, 217 reviews

New:Cozy Barn-Style Retreat Minutes From Woodstock

Recently featured in Vogue as one of “The Best Airbnbs in Upstate New York for a Weekend Away From the City” - A cozy getaway upstate on 2 acres of beautiful Catskill land. It's only 8 minutes to Woodstock, 5 minutes to the village of Saugerties, and there’s hiking, skiing and swimming within minutes. The entire second floor has been newly renovated including the bathroom and both bedrooms. The first floor is an open layout with kitchen, living and dining areas leading to the backyard deck.

2 – 9 Oct

$3,533 AUD total

Guest favourite

Cottage in Woodstock

4.9 out of 5 average rating, 376 reviews

Famous Architect - Streamside Cottage w/ hot tub

Magical cottage nestled in the woods along the Sawkill River just outside historic Woodstock, NY. Designed by famed architect/author, Lester Walker, this 'Tiny House' is the perfect retreat. You'll be tucked away on 6 secluded acres in the middle of a forest. Hike the grounds, enjoy the river, or stroll the garden. Experience the 2 things that are difficult to find anywhere near a city; silence and stars... Listen to the gentle rapids of the river next to you as you drift off to sleep...

24 – 31 July

$2,295 AUD total

Guest favourite

Cottage in Woodstock

4.9 out of 5 average rating, 399 reviews

Hidden Pines - Downtown Woodstock by Millstream!

Two blocks from Downtown Woodstock tucked away on a quiet lane sits Hidden Pines, a classic Woodstock Cottage. No need for a car here! Spacious light filled rooms and a bluestone terrace provide a soothing respite. Stroll down for a swim at the Millstream which is 1/2 block away. This cottage has been lovingly renovated and includes Central AC and heat. Please note this is a guest house. The main house is quietly owner occupied with its own private separate side yard.

12 – 19 Sept

$2,517 AUD total

Guest favourite

Cottage in Saugerties

4.93 out of 5 average rating, 217 reviews

Chic & Cozy Cottage 10 mins to Woodstock

Located on a bucolic country road on the border between Saugerties and Woodstock, this newly renovated 500 sq ft cottage is on a private acre filled with spaces to relax: screened in dining shed, fire pit, BBQ grill, a creek, forest & the magical sound of a hidden waterfall across the road. Just 10 min from Woodstock town square, 8 min to Levon Helm Studios, and 15 from Bearsville Theater, it's the perfect escape. (Pets welcome on a case by case basis. Please ask.)

22 – 29 Sept

$1,551 AUD total

Guest favourite

Cottage in Phoenicia

4.94 out of 5 average rating, 225 reviews

Cozy Catskill Cottage on the Pantherkill

Cozy Cottage nestled in the Catskill Mountains minutes away from village of Phoenecia. This is a great secluded spot and easy to get to and conveniently located near great restaurants, skiing, hiking, tubing, fishing, swimming holes, Village of Woodstock. This small cottage feels bigger than it is while remaining cozy and intimate. Great getaway spot for couples or a solo retreat into the beautiful Catskill Mountains. License #2022-STR-AO-084

9 – 16 July

$2,164 AUD total

Guest favourite

Cottage in Saugerties

4.97 out of 5 average rating, 129 reviews

Cozy Cottage, just off exit 20, 1/2 hr to Hunter

We welcome you to this newly constructed, 1 bedroom, 600 sq ft custom carriage house. Eat in kitchen contains all modern amenities, Queen adjustable bed, high speed internet, 55” Roku TV, All of which is located 1/2 mile from NYS Thruway, 1 mile from Village of Saugerties, 2.5 miles to HITS, 9 miles to Woodstock, 20 miles to ski Hunter, Windham This property offers plenty of parking and enough room to accommodate trailers if necessary.

17 – 24 Jan

$1,733 AUD total

Guest favourite

Cottage in Shokan

4.9 out of 5 average rating, 241 reviews

Catskills 2 br Cottage

This sunny, 2br 1.5 bath cottage is perched on a mountainside, so you can enjoy the seasonal view of the Catskill Mountains and the Ashokan Reservoir as you bask in the warmth of the woodstove and cook great meals in the fully equipped kitchen. Located on a quiet, dead-end road, it is close to Woodstock and Phoenicia and less than 30 minutes from skiing at Belleayre. Just a 2-hour drive from NYC!

23 – 30 July

$1,593 AUD total

Guest favourite

Cottage in Bearsville

4.99 out of 5 average rating, 143 reviews

Coldbrook Cottage

Welcome to Coldbrook Cottage. A great romantic get-a-way. All 5-STAR reviews. We offer the amenities of a great hotel suite, but totally private. It's on one of Woodstock's nicest roads for walking, jogging, and bicycling. Wilson State Park is across the street and we're surrounded by protected land. 8 minutes to Woodstock. 20 minutes to Kingston. 20 minutes to skiing . Check our reviews!

12 – 19 Jan

$2,289 AUD total

Guest favourite

Cottage in Woodstock

4.95 out of 5 average rating, 258 reviews

Woodstock Streamside Cottage

Our streamside cottage is located on a five acre property walking distance to the center of Woodstock. The Sawkill Stream is your backyard with plenty of beautiful trees and meadows your front yard. Quiet sounds of the stream and nature surround you. Central heat and central a/c keeps you comfortable year round. Newly renovated. Please read our reviews and see how you'll feel. Enjoy!

27 Jan – 3 Feb

$3,098 AUD total

Holiday rentals for every style

Get the amount of space that is right for you

Apartments

Convenient locations with everyday essentials

Houses

A space that's all yours, with room for everyone

Cabins

Kick off your hiking boots at these rustic lodgings

Popular amenities for Woodstock cottage rentals

Free parking on premises

Air conditioning

Cottage rentals with a hot tub

Guest favourite

Cottage in Phoenicia

4.89 out of 5 average rating, 801 reviews

Romantic hot tub cottage. Hiking/breweries nearby.

1 – 8 Oct

$2,114 AUD total

Guest favourite

Cottage in Red Hook

4.92 out of 5 average rating, 324 reviews

Goose Landing Cottage by the lake with NEW Hot Tub

24 – 31 Jan

$2,760 AUD total

Guest favourite

Cottage in West Hurley

4.94 out of 5 average rating, 251 reviews

Woodstock Carriage House HotTub FirePit Pool

7 – 14 Oct

$2,729 AUD total

Cottage in Kerhonkson

4.84 out of 5 average rating, 141 reviews

Gunks Cottage|Fire Pit|Pool|Near Minnewaska Park

15 – 22 Jan

$4,025 AUD total

Guest favourite

Cottage in Andes

4.97 out of 5 average rating, 100 reviews

Secluded Romantic Cottage close to Ski Areas

23 – 30 Sept

$2,108 AUD total

Guest favourite

Cottage in Mongaup Valley

4.98 out of 5 average rating, 159 reviews

Hot Tub, Playground, 3 Acres, and Much More!

28 Sept – 5 Oct

$3,074 AUD total

Cottage in Denver

4.96 out of 5 average rating, 110 reviews

Country Cottage w/ HOT TUB & Views

18 – 25 June

$5,054 AUD total

Guest favourite

Cottage in Glen Spey

4.87 out of 5 average rating, 158 reviews

Charming cottage with Hot Tub -PET FRIENDLY

12 – 19 Oct

$1,742 AUD total

Pet-friendly cottage rentals

Guest favourite

Cottage in Woodstock

4.83 out of 5 average rating, 212 reviews

Woodstock Cottage In Town with large yard for pets

22 – 29 Nov

$2,625 AUD total

Guest favourite

Cottage in Kerhonkson

4.91 out of 5 average rating, 379 reviews

Home Alone Woods

31 July – 7 Aug

$1,764 AUD total

Guest favourite

Cottage in Saugerties

4.98 out of 5 average rating, 183 reviews

Chic cottage retreat: Saugerties/Woodstock & HITS.

29 Sept – 6 Oct

$2,204 AUD total

Guest favourite

Cottage in Tannersville

4.9 out of 5 average rating, 207 reviews

Spruce House on Gooseberry Creek

25 Sept – 2 Oct

$1,725 AUD total

Guest favourite

Cottage in Phoenicia

4.93 out of 5 average rating, 214 reviews

Charming creekside cottage in Phoenicia

17 – 24 Sept

$2,154 AUD total

Guest favourite

Cottage in Catskill

4.96 out of 5 average rating, 232 reviews

1930's Cottage charm air conditioned near hiking

17 – 24 Mar

$1,102 AUD total

Guest favourite

Cottage in Bloomington

4.98 out of 5 average rating, 469 reviews

'The Blue Jay Cottage' - Privacy With A View!

12 – 19 July

$2,023 AUD total

Guest favourite

Cottage in High Falls

4.99 out of 5 average rating, 410 reviews

Sun Cottage- "A view with a room(s)."

20 – 27 July

$3,893 AUD total

Private cottage rentals

Guest favourite

Cottage in Bearsville

4.98 out of 5 average rating, 148 reviews

Mirror Moon Cottage (waterfront)

7 – 14 June

$2,607 AUD total

Guest favourite

Cottage in Saugerties

4.98 out of 5 average rating, 178 reviews

Blue Mountain Cottage

8 – 15 June

$1,936 AUD total

Guest favourite

Cottage in Kingston

4.81 out of 5 average rating, 146 reviews

Cottage w/ Deck @woodstockwellnessplace

9 – 16 July

$1,662 AUD total

Guest favourite

Cottage in Saugerties

5.0 out of 5 average rating, 314 reviews

Carriage House on Falls, Walk to Village

6 – 13 Oct

$3,167 AUD total

Guest favourite

Cottage in Rhinebeck

4.99 out of 5 average rating, 121 reviews

Fabulous Lemon Cottage in Rhinebeck, NY

12 – 19 July

$2,557 AUD total

Guest favourite

Cottage in Roxbury

4.98 out of 5 average rating, 481 reviews

The Little House

22 – 29 Nov

$1,392 AUD total

Guest favourite

Cottage in Kerhonkson

4.94 out of 5 average rating, 257 reviews

Blue Haven in the Catskills

8 – 15 Sept

$1,286 AUD total

Guest favourite

Cottage in Tillson

4.99 out of 5 average rating, 107 reviews

Cozy cottage with local art

28 Oct – 4 Nov

$1,929 AUD total

Quick stats about cottage rentals in Woodstock

Total rentals
20 properties
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Pet-friendly rentals
10 properties allow pets
Family-friendly rentals
10 properties are a good fit for families
Total number of reviews
4.1K reviews
Nightly prices starting at
$167 AUD before taxes and fees

Destinations to explore