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Vacation rentals with a pool in Crawford

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Crawford

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Cottage in Pine Bush

4.89 out of 5 average rating, 228 reviews

Seclusion and romance and free drinks!

Amazing 5 Star guest house. Free electric car charging both telsa and all others! Outdoor living room with a wood fireplace. Close to many Hudson Valley attractions: hiking, wineries, breweries, restaurants, Sam's Point, etc. Very romantic, high end getaway. Amenities: charcoal BBQ, mini fridge, propane grill, full bath, microwave, wood fireplace, fire pit, single induction hot plate, wifi, smart TV, Firewood and fire bricks available. The pool will be closing the week of October 16th 2023.

Jan 17 – 24

R5,796 ZAR per night

Home in Middletown

4.94 out of 5 average rating, 100 reviews

Springtime farm escape with hot tub and amenities

Looking for a perfect Winter upstate retreat? Look no further! Welcome to our beautiful 100 year old farmhouse! Nestled on over two acres in the Southern valley of the Shawangunk mountains, this is a beautiful area to explore foliage and hikes, stay home to soak in the hot tub, warm up by the fireplace, or cook! We are located in the Sullivan County Catskill region, next to the Hudson Valley and Delaware River regions. With farmland and hiking nearby, we know you will love this beautiful area.

Jul 25 – Aug 1

R4,090 ZAR per night

Home in Stormville

4.94 out of 5 average rating, 156 reviews

Private Hudson Valley Country Retreat

Beautiful 1930s house set on 18 private acres of land overlooking a private lake. Immaculately landscaped surrounding area with koi and gold fish pond with a waterfall, gazebo, hammock and most importantly untouched nature. Very private! Enjoy your morning coffee or tea in the outdoor covered patio overlooking the property, wine and dine under the pergola, enjoy the fire pit or wood burning fireplace on a chilly evening. Serenity and relaxation at its best! Pond dock coming up in Spring of 2021

Dec 28 – Jan 4

R14,867 ZAR per night

Home in Cold Spring

4.95 out of 5 average rating, 152 reviews

Cozy, Modern Retreat in the Woods of Cold Spring

Newly renovated with modern style and amenities yet retaining all of its rustic warmth and charm, our home is perfect for your next get away. Outdoors, enjoy the salt water pool, patio, grill and fire pit in our secluded setting. Indoors we offer a sauna, steam shower, central heat and air, a woodburning fire place, crib and baby monitor, ping pong table, washer and dryer, and a fully loaded kitchen. Located 7 minutes drive from charming Cold Spring and just across the river from West Point.

Mar 19 – 26

R10,233 ZAR per night

Cottage in Kerhonkson

4.85 out of 5 average rating, 142 reviews

Gunks Cottage|Fire Pit|Pool|Near Minnewaska Park

This charming 2-bedroom cottage is nestled on an acre of private, untouched wilderness, making it a great place for nature lovers, hikers, and couples looking for the perfect getaway. When you’re not exploring Minnewaska State Park, enjoy the pool, stargazing from next to the fire pit, and soaking tired muscles in the hot tub. 6 Min Drive to Minnewaska State Park Preserve 10 Min Drive to Stony Kill Falls 15 Min Drive to Wightman Fruit Farm Experience Kerhonkson With Us & Learn More Below!

Jan 18 – 25

R5,680 ZAR per night

Home in New Paltz

4.98 out of 5 average rating, 437 reviews

midcentury modern in ground pool walk 2 trail/town

A Frank Lloyd Wright inspired Mid Century Mod w updated amenities, comfy, clean, open concept. Large windows offer big views of flora/fauna and the many birds & wildlife. Mtn views including skytop. short wooded trail just behind house to access Wallkill Valley Rail Trail, from here walk a scenic mile to R2R trail Water St. mkt & the ❤️ of New Paltz Village. Several outdoor seating areas. The whole place is yours FULL PRIVATE ACCESS TO HOUSE/PROPERTY POOL OPEN MAY 1 - end of SEPTEMBER

Jun 3 – 10

R12,133 ZAR per night

Home in Woodstock

4.98 out of 5 average rating, 101 reviews

Woodstock Historic Artist Estate- The Museum House

The property is an estate formerly owned by renowned artist Reginald Marsh located within a 10 minute walking distance to the center of the historic town of Woodstock, NY. The 2500sft house is the former Museum House that used to hold Mabel Marsh’s art collection that was later acquired by the Smithsonian Institute. It has been architect gut-renovated into a dramatic living experience surrounded by nature and water. The Pond and Carriage House are at the opposite side of the estate..

Nov 25 – Dec 2

R17,504 ZAR per night

Home in Kerhonkson

4.94 out of 5 average rating, 325 reviews

Country House: Rustic Charm With Modern Feel

Look from the luxurious spa tub at the countryside oasis atop a rolling knoll on the edge of fir-scented forest land. Come home from a hike, farm, or award winning restaurant, & snuggle up by the fire under grand cathedral ceilings. In summer, swim in the salt water pool & enjoy the fire pit surrounded by lush landscaping & quiet. Stunning views as the seasons change, the windows showcasing rolling snowy hills or the vibrant colors of autumn leaves climbing the mountains.

Sep 10 – 17

R11,609 ZAR per night

Guesthouse in Margaretville

4.99 out of 5 average rating, 134 reviews

Sunny Arts & Crafts Loft

Catskill Mtn. Summer: hiking, swimming, relaxing. Explore fun towns like Margaretville, Andes & more. May & June are almost fully booked, but lots of great summer and fall dates available. Situated on a peaceful mountainside, the loft is a cozy, private place to unwind as you enjoy a Catskill Mtn. adventure. Super savings on longer stays, too! Our road is plowed & sanded, but you will definitely need AWD & good tires to ensure smooth travels in the WINTER months.

Feb 12 – 19

R1,885 ZAR per night

Chalet in Olivebridge

4.98 out of 5 average rating, 124 reviews

Spruced Moose Lodge & Treehouse w. Hot Tub & Pool!

Secluded log home on 5 acres, beautifully situated at the top of a no outlet road on a mountainside in the Catskills. The home has 4 bedrooms + 3.5 baths, with the 4th bedroom being a finished basement that has built-in full size bunk beds. There is also a sunroom, screened porch, pool, hot tub, and a treehouse that resembles a floating pirate ship 30 feet up in the trees. Town of Olive Registration No: STR-23-2 SEC-BLK-LOT: 52.4-1-5.500

Sep 30 – Oct 7

R12,561 ZAR per night

Loft in Cornwall

4.86 out of 5 average rating, 395 reviews

Country Getaway - Close to Hiking & Storm King

Enjoy the countryside in our private, cozy loft studio! Located on 1.5 acres, this clean and comfortable apartment includes a kitchenette with bar-style table, living room and flat screen Roku TV with Netflix, Hulu as well as an electric fireplace, outdoor patio and fire pit. Guests have their own parking space, a private first-floor entrance, full bathroom, patio, BBQ and fire pit!

Dec 8 – 15

R1,689 ZAR per night

Cabin in Red Hook

4.96 out of 5 average rating, 306 reviews

Modern Upstate Cabin, near Rhinebeck NY

🏊🏽‍♂️Heated pool is open. (Will be winterized mid October Welcome to Maitopia. This beautifully designed passive glass and wood modern cabin offers elegant modern details and the warmth that only an upstate energy efficient retreat could. With a soaking egg tub, fires at every turn and a heated pool you will fall in love with the place and the towns nearby.

Aug 22 – 29

R8,627 ZAR per night

Vacation rentals for every style

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Popular amenities for Crawford rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

Home in Stamford

4.97 out of 5 average rating, 220 reviews

Midcentury Modern ZenHouse Sculptor Studio

Dec 15 – 22

R7,141 ZAR per night

Home in West Milford

4.99 out of 5 average rating, 113 reviews

On The Rocks In The Hot Tub

Oct 1 – 8

R8,085 ZAR per night

Home in Narrowsburg

4.97 out of 5 average rating, 141 reviews

Modern Ranch With Pool & Hot-Tub

Sep 28 – Oct 5

R9,032 ZAR per night

Home in Downsville

4.97 out of 5 average rating, 110 reviews

Trout fishing on the Delaware

Jan 10 – 17

R2,811 ZAR per night

Home in Pound Ridge

5.0 out of 5 average rating, 126 reviews

Peaceful Light-Filled Guesthouse 1 Hour From NYC

Dec 14 – 21

R12,922 ZAR per night

Home in Cottekill

4.95 out of 5 average rating, 242 reviews

Peace & Privacy - High Falls (hot tub & salt pool)

Dec 20 – 27

R6,715 ZAR per night

Home in New Paltz

4.93 out of 5 average rating, 121 reviews

Harrison Field 50% Off 3rd Night Mother’s Day WKND

Jan 3 – 10

R14,272 ZAR per night

Home in Putnam Valley

4.93 out of 5 average rating, 182 reviews

Putnam Valley Escape

Oct 2 – 9

R12,084 ZAR per night

Condo rentals with a pool

Condo in Vernon Township

4.76 out of 5 average rating, 137 reviews

1 Bedroom Condo @ Appalachian Resort Hotel

Sep 27 – Oct 4

R2,697 ZAR per night

Condo in Vernon Township

4.95 out of 5 average rating, 732 reviews

Appalachian Lodge Top Floor w/views

Sep 16 – 23

R3,473 ZAR per night

Condo in Vernon Township

4.97 out of 5 average rating, 217 reviews

Rustic Chic at Mountain Creek! Pool|Hot Tub|Sauna

Nov 21 – 28

R4,127 ZAR per night

Condo in Vernon Township

4.95 out of 5 average rating, 239 reviews

NYC Escape 1 hr away

Oct 8 – 13

R4,252 ZAR per night

Condo in Vernon Township

4.94 out of 5 average rating, 104 reviews

Resort Getaway-Mtn Creek Ski/Pool/Hot Tub/Sauna

Oct 31 – Nov 7

R3,742 ZAR per night

Condo in Vernon Township

4.9 out of 5 average rating, 203 reviews

Upscale Condo Ski-In/Out Mountain Creek 1 hr NYC

Dec 4 – 11

R3,352 ZAR per night

Condo in Vernon Township

4.87 out of 5 average rating, 177 reviews

Newly renovated bright and open 1 bedroom

Feb 5 – 12

R3,292 ZAR per night

Condo in Vernon

4.94 out of 5 average rating, 125 reviews

Mtn front Resort Pool Hot Tub Sauna Best View 340

Sep 2 – 9

R6,388 ZAR per night

Home rentals with a private pool

Home in Lagrangeville

4.84 out of 5 average rating, 120 reviews

Classic Hudson Valley Farmhouse Nestled in 9 Rolling Acres

Oct 22 – 29

R11,400 ZAR per night

Home in Woodstock

4.6 out of 5 average rating, 10 reviews

Luxury Retreat in the Catskills

Sep 2 – 9

R21,131 ZAR per night

Home in Lanesville

4.77 out of 5 average rating, 205 reviews

Go Hiking and Skiing from a Family-Friendly Farmhouse

Mar 15 – 22

R7,897 ZAR per night

Home in Rhinebeck

5.0 out of 5 average rating, 65 reviews

Rhinebeck Country Living with a Modern Twist

Oct 4 – 11

R11,712 ZAR per night

Home in East Stroudsburg

New place to stay

Pocono Escape - Cozy 5br - Sauna-Billiard

Dec 31 – Jan 7

R18,062 ZAR per night

Home in East Stroudsburg

New place to stay

Open Concept-Hottub-Sauna-Billiard-Poker

Oct 2 – 9

R11,549 ZAR per night

Home in East Stroudsburg

New place to stay

Cozy Affordable Family Place In Poconos

Jun 10 – 17

R7,846 ZAR per night

Destinations to explore