
Holiday rentals with a pool in Ashland
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Ashland
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

1940s Vintage apartment steps from the Rogue River
Welcome one and all to DunMovin'. At Riverside on the Rogue you will go to sleep with views of the stars through the skylights and wake up to the Wild and Scenic Rogue just outside your French Doors. Throw a line in and fish from the yard if you like. Lounge by the heated saline pool, feed the geese, go shopping, or head to any of our amazing local restaurants. I'm in the city limits. It's my slice of heaven and I'm sharing it with you. My other unit can be found at: 'The Cottage at DunMovin'

The Green Arrow Loft
Situated right on the state line this studio apartment is nestled in its own little corner of the gorgeous Colestine Valley. We're located on 80 acres that adjoin the Cascade-Siskiyou National Monument to the north, perfect for a scenic hike or a casual stroll. Nature and wildlife abound, and though quiet and private the Loft is just five minutes off I-5 and 25 minutes from unique downtown Ashland. We're pet friendly and have an outdoor pool! See the House Rules for details on pet and pool fees.

Tiny Groove with plunge pool and soaking tubs
A unique off grid experience awaits you at our eco-friendly solar powered tiny home on 6 secluded acres. The home site is perfectly cut into a groove in the hillside 200 feet above the valley below allowing for beautiful Mountain views and amazing privacy with no visible neighbors other than the variety of local wildlife. Enjoy the outdoor soaking tubs, wood fired sauna and a seasonal plunge pool. Just a short 5 minute drive to the lovely town of Rogue River and access to I-5. Pet friendly too!

Perfect 4 Work Crews! Pool Table, Spa, big TV’s
Perfect for Work Teams or Families to build lasting memories. Private home in Beautiful Scenic Medford Foothills! Close to everything, but out of town. Nearby dining and groceries. Quick drive to Ski Ashland, Crater Lake, Water Ski Lakes, Fishing Lakes, and Roxy Ann Winery. Hiking at Roxy Ann and Table Rocks. Vaulted Great Room, huge modular couch, 65" and 75" TVs, Redzone, Pool Table, Ping Pong, Coffee & Wine Bar, Golden Tee. Year-Round Hot Tub, Seasonal Swimming Pool (mid May-End of Sept.)

Mexico Apartment at Wood Hamlet, by Downtown
The Wood Hamlet Mexico Apartment is a delightful space filled with color and culture. A short walk to town, 72-acre park & the theaters. Feel the welcoming warmth of the hand-crafted Mexican decor. Basement unit but with lots of windows and light. (4 beams at 6'1") Kitchen, with top of the line induction burner, fridge, microwave..., full bath, W/Dryer, work area... Wi-fi. Beautiful, garden with sitting areas & swimming pond. Parking. (Ashland City Permit# 17-080) NO SMOKING ON PREMISES

Tiny Cabin in the Woods | Hot Tub & Alpaca Rescue
Enjoy the charm of staying in a Tiny forest cabin, surrounded by nature and stylishly decorated with thoughtful décor accents. This is a tiny cabin, but has all the essentials that you need for your stay. Great location on the outskirts of town (8 mins from Merlin & 15 mins from Grants Pass). The closest access to the river is only 10 mins away at Matson Park! After a day of exploring, enjoy your hot tub with a wooded view or stargaze by the shared fire pit. Perfect Couples little getaway!

The Aloha House - Hot Tub - Pool
The Aloha House is located just above the University and only 1.5 miles from downtown Ashland. Nestled up a hill in the forest, you'll be transported to your own little private resort-like getaway with stunning views, architectural design that brings the outdoors in, and ample space for dining and entertaining poolside. The property consists of two separate studios (both included) connected by a unique outdoor living space with a seasonal pool, spa, outdoor shower, bar & BBQ, and more!

Scenic and relaxing roadtrip stop-over!
This is a scenic stop between PDX and SF and its own destination. One guest says " Her home has a magic of its own." Simple, elegant, and a great base for wine-tasters, paraglider, or roadtrippers. If a house surrounded by nature, vineyards, paraglider pilots, creativity and occasional other travelers sounds interesting, you'll love it here. As a local tourism coordinator, I can direct you to the top attractions. Note: this is a self-contained unit but attached to the main house!

Octagon Studio / Beautiful Rogue River property
Park-like setting; Rogue River premier property. Use the Octagon Studio to enjoy the luxuries of the property or as a home base for the many amenities in the Rogue Valley. Relax by the pool or soak in the hot tub, lounge on the rivers beach, watch the river go by from the floating dock(seasonal) swing between two large pine trees, have an evening fire in the fire pit, catch trout for a morning breakfast, watch the abundant wildlife. Relaxing, romantic, fun, resort quality....enjoy

Broken Chair Ranch
Welcome to the beautiful Griffin Creek area just outside of Medford, Jacksonville, and Ashland. Our home is at the top of a hill with stunning views of the city lights as well as upper and lower Table Rock. Enjoy the hot tub and watch the sunset with the fire pit on the front porch. The house is on 40 acres and has a gorgeous view at the top with a stunning echo off the mountain Private setting one mile up a gravel road, 2wd friendly

Sunset View Yurt of Applegate Valley with HOT TUB!
NO CLEANING FEE! Large 24 ft yurt located on our 5 acre property. Gorgeous views to the west. Includes a king size bed, and queen sofa bed. Located in Applegate Valley. Many fabulous wineries nearby. We're 6 miles south of downtown Grants Pass, and 2 miles north of Murphy. Enjoy the hot tub under the stars, or catch a spectacular sunset. It's all good! Please note: Well behaved, non destructive children are welcome.

Peace on the Rogue river Studio
Beautiful park like setting on the Rogue river with a jacuzzi, swim spa two decks, fishing, yard games, hammock, barbecues, bicycles, kitchenette has Keurig With pods,a toaster oven, crock pot, small George Forman a portable two burner cook top , small skillet, one pot and most utensils to provide a meal. Minutes from Grants Pass, shopping, restaurants, and winery's.
Popular amenities for Ashland rentals with a pool
House rentals with a pool

Cherry Lane, Crystal Skies

Medford White House

Jacksonville Mountain Retreat!

Capital House - Private getaway with POOL!

Entertainment Home on Golf Course - Hot Tub /Pool

Fantastic Bright 4 Bedroom- Deck - Fireplaces

Poolside Retreat W/ Sauna Heart of Wine Country

Luxury Stay: Pool • Spa • Sauna
Other holiday rentals with a pool

Cozy Condo in East Medford w/ Pool and Hot Tub

Eagle Point Golf Retreat: Pool Access + Patio!

3BR House with pool, Near Hospital

Stunning East Medford studio with pool & hot tub

The Siskiyou House

Hillcrest House LLC - The Main Residence

Be Our Guest at The Sunrise Guest House

County Farmhouse, Perfect for Large Gatherings
When is the best time to visit Ashland?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $147 SGD | $124 SGD | $129 SGD | $134 SGD | $206 SGD | $217 SGD | $217 SGD | $217 SGD | $217 SGD | $197 SGD | $158 SGD | $181 SGD |
| Avg. temp | 5°C | 7°C | 9°C | 12°C | 16°C | 19°C | 24°C | 24°C | 20°C | 13°C | 7°C | 4°C |
Quick stats about holiday rentals with a pool in Ashland

Total holiday rentals
Explore 20 holiday rentals in Ashland

Nightly prices starting at
Ashland holiday rentals start at $52 SGD per night before taxes and fees

Verified guest reviews
Over 1,300 verified reviews to help you choose

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
20 of Ashland holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Ashland rentals

4.8 Average rating
Ashland stays are highly rated by guests – averaging 4.8 out of 5!
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