Updating...

Enter dates for more accurate prices

Woodstock Rentals

Filter

Woodstock Rentals

About Woodstock

40 apartments

$295

Tranquil Woodstock Home in the Woods with Hot Tub and Ping Pong

Woodstock house

2 bedrooms / 2 bathrooms / sleeps 4

$295

1 / 14

$315

Woodstock Cottage: walk to Town

Woodstock cottage

2 bedrooms / 3 bathrooms / sleeps 4

“Very well kept and extremely caring owners” The cottage seems as though it was renovated yesterday because it is so clean and well kept. The kitchen has everything you need to cook, and the living room is comfortable. There are many games and movies a

Responds fast! avg. 3 hours 50 minutes

$315

1 / 22

$150

Woodstock In-town cottage

Woodstock cottage

1 bedroom / 1 bathroom / sleeps 2

“Perfect” This little gem was the perfect getaway for me, my friend and my dog Amber. The location was private yet walking distance into town, near a beautiful stream and gentle, peaceful hiking trails. The owners El and Eric personally met us when we

Responds fast! avg. 10 minutes

$150

1 / 23

$155

Teahouse Cottage

Woodstock cottage

50 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 3 hours 0 minutes

$155

1 / 13

$165

Margaret's Cottage in Woodstock Village

Woodstock log cabin

2 bedrooms / 1 bathroom / sleeps 4

$165

1 / 29

$190

Schoolhouse Cottage

Woodstock house

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 3 hours 0 minutes

$190

1 / 14

$249

Sun Salutations in Woodstock, a mile to the village & a stop on Trailways

Woodstock house

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 2 hours 8 minutes

$249

1 / 25

$500

Chic Retreat in Bearsville 2 m to Woodstock, Saline Pool, Fireplace and Hot tub.

Woodstock house

2 bedrooms / 3 bathrooms / sleeps 6

“Clean & Comfortable... Quiet & Relaxing...” My wife, 2 dogs and I very much enjoyed our 3 day stay here at the Bearsville Retreat. We arrived on the morning of Super Bowl Sunday, skied Belleayre with friends, had a nice dinner in Woodstock and then ca

$500

1 / 55

$260

JUNE SALE! Jun 14-17 $230/night at Pet Friendly Cabin Doh-Ray Up At 1450ft

Woodstock house

2 bedrooms / 2 bathrooms / sleeps 5

“Relaxing mountain retreat” We enjoyed a very pleasant Thanksgiving week getaway at the cabin, which looks just like the pictures -- nice combination of modern and rustic design. Also very comfortable, clean and well organized. Tv and sound system very

Responds fast! avg. 2 hours 34 minutes

$260

1 / 30

$225

Woodstock Village Serene & Spacious

Woodstock house

2 bedrooms / 1 bathroom / sleeps 6

$225

1 / 10

$450

Stunning Vacation Country & Ski House

Woodstock house

4 bedrooms / 3 bathrooms / sleeps 10

“One of a kind, secluded, comfortable, & friendly.” We had the best weekend here in this beautiful spacious house. The huge windows all around the living area give such a peaceful feeling looking at the forst or the stream in the backyard. We enjoyed f

Responds fast! avg. 2 hours 17 minutes

$450

1 / 23

$500

Woodstock Secluded MT Top Home with Swimming pool

Woodstock house

6 bedrooms / 3 bathrooms / sleeps 15

$500

1 / 9

$100

A Little Woodstock Love Nest. Walk to everything!

Woodstock apartment

1 bedroom / 1 bathroom / sleeps 4

$100

1 / 18

$255

Spacious Family Retreat, Woodstock, 2hrs from NYC

Woodstock house

4 bedrooms / 3 bathrooms / sleeps 9

$255

1 / 17

$475

Mountain Woodland Private Elegant Peacefull MAGIC

Woodstock house

3 bedrooms / 3 bathrooms / sleeps 6

$475

1 / 15

$220

Olive Oasis Luxury with Hot Tub, Woodstock Area

Woodstock house

3 bedrooms / 2 bathrooms / sleeps 6

“A true escape into nature and solitude!” Olive Oasis is a true gem in the gorgeous area of the ashokan Reservoir and Catskill Mountains. The home is uniquely and tastefully decorated and impeccably clean with an open and spacious layout. Large kitch

$220

1 / 26

$295

Woodstock Stone Cottage Swim Lake 3 ski resorts fishing hiking biking music arts

Woodstock house

4 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 2 hours 3 minutes

$295

1 / 22

$1,000

Woodstock Peace, Privacy, Views

Woodstock house

4 bedrooms / 5 bathrooms / sleeps 9

$1,000

1 / 17

$395

Classic Mid-Century Modern in Woodstock, 5 minutes from town.

Woodstock house

5 bedrooms / 4 bathrooms / sleeps 8

$395

1 / 6

$198

Glamping at Woodstock Meadows - Outdoor B&B (2 secluded tents w/amenities)

Woodstock tented camp

2 bedrooms / 1 bathroom / sleeps 4

$198

1 / 4

$195

Romantic Country Barn By the Stream

Woodstock log cabin

2 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 47 minutes

$195

1 / 26

$225

2 BR Cabin, Hot Tub, Fireplace, Heart of Woodstock

Woodstock log cabin

2 bedrooms / 1 bathroom / sleeps 6

Responds fast! avg. 1 hour 32 minutes

$225

1 / 20

$250

Secluded, Luxury Home with Hot Tub

Woodstock house

2 bedrooms / 2 bathrooms / sleeps 6

“Simply the best!” Before we even explored the beautiful house and the perfect location, we thought 'We are home'. This wonderful property is possibly the nicest, most pristine clean and convenient house we've had the pleasure to stay in. It is wonderf

Responds fast! avg. 1 hour 32 minutes

$250

1 / 19

$225

Marigold cabin by the stream - Heart of Woodstock with Hot Tub & Fireplace

Woodstock cottage

1 bedroom / 2 bathrooms / sleeps 4

Responds fast! avg. 1 hour 29 minutes

$225

1 / 27

$325

Woodstock gorgeous cottage & pool. on 10 acres

Woodstock house

2 bedrooms / 1 bathroom / sleeps 6

$325

1 / 19

$200

Cozy & Serene Cottage in Woodstock

Woodstock cottage

1 bedroom / 1 bathroom / sleeps 3

$200

1 / 13

$450

Woodstock Mediterranean Retreat

Woodstock house

4 bedrooms / 3 bathrooms / sleeps 11

Responds fast! avg. 3 hours 49 minutes

$450

1 / 26

$115

Woodstock Town Center Studio Apt.

Woodstock apartment

1 bedroom / 1 bathroom / sleeps 2

$115

1 / 8

$200

Woodstock Carriage House

Woodstock house

4 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 33 minutes

$200

1 / 14

$425

Charming Converted Barn On 2+ Acres Walk To Town

Woodstock house

5 bedrooms / 2 bathrooms / sleeps 10

$425

1 / 14

$450

New Hot Tub & Heated Pool in Prime Woodstock Gut Renovated Modern Home

Woodstock house

5 bedrooms / 3 bathrooms / sleeps 13

Responds fast! avg. 30 minutes

$450

1 / 82

$150

Sioux Tipi on the waterfall

Woodstock tipi/teepee

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 3 hours 0 minutes

$150

1 / 12

$350

Mid Century Ranch-Hot Tub-Minutes to Center ofTown

Woodstock house

4 bedrooms / 4 bathrooms / sleeps 8

Responds fast! avg. 2 hours 8 minutes

$350

1 / 36

$350

Woodstock Modern House with a Pool

Woodstock house

4 bedrooms / 2 bathrooms / sleeps 10

$350

1 / 37

$170

Charming Artist's Cottage

Woodstock house

2 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 1 hour 46 minutes

$170

1 / 18

$295

Woodstock Retreat, Sauna, Steam Shower, Decks

Woodstock house

2 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 2 hours 55 minutes

$295

1 / 22

$295

Woodstock-Pool, Hot Tub, Stream; 7 Acres; Hike&Ski

Woodstock house

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 2 hours 10 minutes

$295

1 / 33

$96

A Little Woodstock Love Inn. Walk to everything!

Woodstock apartment

1 bedroom / 1 bathroom / sleeps 4

$96

1 / 18
Viewing 38 of 40

About Woodstock

×

With a surprisingly large arts community, rolling green hills, and friendly locals, the small and picturesque town of Woodstock has it all! The primary street that hosts a row of boutiques and charming restaurants is known as Tinker Street, but don't limit yourself to this one area. There are plenty of things to see and do across the entire town.

Here are just a few additional suggestions of things to do in Woodstock:

  • Shawangunk Mountains: This mountain range attracts people from all over the area with its rock climbing, hiking, and camping options.
  • SweetHeart Gallery: Overlooking a beautiful waterfall, this popular local gallery features artwork and crafts pieces from some of the best artists in the region.
  • Karma Triyana Dharmachakra Tibetan Buddhist Monastery: This beautiful and serene monastery is the perfect place to spend an afternoon learning about Buddhism or just simply clearing your head.

For those looking to attend local events and festivals, head to Ulster County, a short drive from Woodstock. In Ulster County you can cheer on the competitors participating in the Shandaken Primitive Biathlon in January, watch the boat rally on the Wallkill River at the New Paltz Regatta in May, or take home a piece of art from one of the best artists in the region at the Woodstock-New Paltz Art and Crafts Fair in September.

Luckily, there's a vacation rental available in Woodstock that has everything you are looking for in a getaway home. Book a luxury condo downtown or rent a secluded cabin in the woods just steps from the mountains for an unforgettable vacation experience.

If you're looking to explore the surrounding area, there are several other towns just outside of Woodstock that make for great day trips. The busy college town of Binghamton and the rolling fields of Oswego can both be reached within an hour by car.

Payment Protection
Your payment for this rental is protected when you pay through FlipKey. Learn more