Ashland, Oregon Vacation Rentals. Book Beach Rentals, Lake Houses, Condos, Cabins, Villas, and Homes in Ashland, Oregon on RentalSaver.com!

Ashland Rentals

From $153 per night (USD)
VRBO
The Indigo Cottage 5 Min walk to Downtown Ashland
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Quaint Cottage. Amazing location 1.5 blocks to Downtown Ashland. Outdoor fire pit and vegetable garden and full kitchen. ...
From $153 per night (USD)
VRBO
From $62 per night (USD)
VRBO
Spacious Historic House one block to downtown in fun neighborhood!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Please see reviews of our other place: vrbo.com/181670 as we don't have any for this place yet. This is a monthly renta ...
From $62 per night (USD)
VRBO
From $211 per night (USD)
VRBO
Quiet Garden Courtyard Studio only 3 blocks from downtown
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
We offer complete privacy and relaxing moments of cozy comforts to all. Enjoy the exquisite courtyard garden setting sur ...
From $211 per night (USD)
VRBO
From $451 per night (USD)
Expedia
Artsy Downtown Historical House: Steps to Shakespeare
Bedrooms:
3
Bathrooms:
2
Sleeps:
4
Summary: **Welcome to The Matriarch Heritage House** Located in the HEART of Ashland. Park your car and walk to all you' ...
From $451 per night (USD)
Expedia
From $560 per night (USD)
VRBO
Swank House on Main St in Ashland
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
<p>Located in Ashland, this welcoming vacation home lets you experience it all. Ashland Library is just steps away and O ...
From $560 per night (USD)
VRBO
From $149 per night (USD)
Expedia
Jazzy B Suite~Historic, eco/dog friendly
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
About this space Victorian home built in 1895, walk to downtown shops, restaurants, Oregon Shakespeare Fest. and Lithia ...
From $149 per night (USD)
Expedia
From $219 per night (USD)
VRBO
Swank House -Downtown Suite- Pet Friendly
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: Walk to all the shops, theaters, restaurants, trails and more. Steps to DOWNTOWN Ashland. All recently updated, ...
From $219 per night (USD)
VRBO
From $246 per night (USD)
Expedia
Moody Ashland Escape: Luxe Suite, Copper Tub
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: Welcome to the Premier Suite @ The Matriarch, a historic heritage property in downtown Ashland. This self check ...
From $246 per night (USD)
Expedia
From $215 per night (USD)
VRBO
Swank Boutique Suites | Double Shower
Bedrooms:
2
Bathrooms:
1
Sleeps:
2
Summary: Swank Boutique Suites | King Suite with Double Shower | Downtown Ashland Experience detailed hospitality and pl ...
From $215 per night (USD)
VRBO
From $214 per night (USD)
Expedia
Affordable Luxury- One block to Downtown
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: Welcome to The Matriarch, a historic heritage property in downtown Ashland. This self check-in style accommodat ...
From $214 per night (USD)
Expedia
From $163 per night (USD)
VRBO
Modern Crash Pad | Pet Friendly | West Wing
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: NEW! Upgraded to KING bed!! A modern suite located steps away from the Ashland conference center and just minu ...
From $163 per night (USD)
VRBO
From $232 per night (USD)
Expedia
The Matriarch| Suite 3 | Pet friendly
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: Everything you need for the perfect Ashland getaway. Steps to award winning restaurants, theatre and plenty of ...
From $232 per night (USD)
Expedia
From $233 per night (USD)
VRBO
Swank Boutique Suites | Deluxe King
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: MOUNTAINS, THEATRE, WINE TIME STEPS TO ALL ASHLAND HAS TO OFFER. STAY AND PLAY AT SWANK HOUSE SUITES. 🔹 1 bl ...
From $233 per night (USD)
VRBO
From $232 per night (USD)
Expedia
Swank Boutique Suites | King with Soaking Tub
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: Swank Boutique Suites | King Suite with Soaking Tub | Downtown Ashland Experience detailed hospitality and plus ...
From $232 per night (USD)
Expedia
From $232 per night (USD)
VRBO
Grand Luxe Suite with Jetted Tub
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: Our PREMIER King Suite featuring large jetted tub to relax and unwind. WE ARE STEPS TO ALL ASHLAND HAS TO OFFER ...
From $232 per night (USD)
VRBO
From $122 per night (USD)
Expedia
Just a half-mile from Ashland's charming downtown!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Available Aug. 28, 2025! 3-story townhouse near downtown. Fully-equipped overlooks a garden: range, dishwasher, refrige ...
From $122 per night (USD)
Expedia
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VRBO
Private and quiet luxury studio suite on three acres overlooking Ashland.
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Located on three acres overlooking Ashland, yet just minutes away from everything Ashland has to offer, this private lux ...
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VRBO
From $859 per night (USD)
Expedia
The Blue Moon House has 5 bedrooms, each with a private bath, plus kitchen, dining and living area.
Bedrooms:
5
Bathrooms:
5
Sleeps:
11
Built in the early 1900's and fully renovated. The Blue Moon House has it all! Five bedrooms offering a king or queen b ...
From $859 per night (USD)
Expedia
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VRBO
Quiet Bellview Retreat Front
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
his is the front half of a large updated older house. It is fully furnished and ready to occupy. Both bedrooms are upsta ...
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VRBO
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Expedia
Quiet Bellview Retreat Rear
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Located on the south edge of Ashland, and set back from the street, this quiet one-bedroom is fully furnished and privat ...
Click For Pricing
Expedia
From $319 per night (USD)
VRBO
Hanna's House | 1 block to downtown!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Welcome to Hanna's House, a one-bedroom retreat just blocks and walking distance from downtown Ashland. Featuring a lu ...
From $319 per night (USD)
VRBO
From $419 per night (USD)
Expedia
Charming house two blocks from downtown Ashland
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
The Serendipity House is a comfortably stylish escape in the heart of Ashland. Our newly remodeled home has all the comf ...
From $419 per night (USD)
Expedia
From $117 per night (USD)
VRBO
Cozy European Cottage 2 bd + 1 bath
Bedrooms:
1
Bathrooms:
2
Sleeps:
2
About this space Kick back and relax in this calm, stylish space. A rental agreement is listed in detail under house rul ...
From $117 per night (USD)
VRBO
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Expedia
Centrally located Historic Home with parking
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Experience history and enchantment at our Ashland, Oregon home built in 1887. Our home is minutes walk to everything and ...
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Expedia
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VRBO
Brand New Crowson Cottage
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
About this space The Crowson Cottage is located in a beautiful private setting, close to many amazing wineries and withi ...
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VRBO
From $311 per night (USD)
Expedia
2 bedroom cabin, huge deck, lodge-style furnishings.
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Premium cabin, huge deck, lodge-style furnishings in an Alpine setting at 5200' elevation, just 18 miles east of downtow ...
From $311 per night (USD)
Expedia
From $426 per night (USD)
VRBO
Barclay Klum House by WanderLodges | Soaking Tub | Gourmet Kitchen
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Introducing the Barclay-Klum House: A meticulously restored 2-bedroom, 1-bath gem, walking distance to Ashland's vibrant ...
From $426 per night (USD)
VRBO
From $202 per night (USD)
Expedia
Hyatt Prairie Cabin offers views and a two person Hot Tub! Both bedrooms have a queen size bed.
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
About this space Welcome to your Hyatt Prairie Cabin with views and a two person Hot Tub! The primary bedroom, located ...
From $202 per night (USD)
Expedia
From $349 per night (USD)
VRBO
1 bedroom, 1 bathroom cottage with sleeper sofa & full kitchen.
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
The Bluemoon Cottage is a perfect getaway for a couple or friends visiting Ashland, OR. The one bedroom (queen bed), one ...
From $349 per night (USD)
VRBO
From $1368 per night (USD)
Expedia
2 units with 6 bedrooms, 6 bathrooms, a kitchen and large dining area.
Bedrooms:
6
Bathrooms:
6
Sleeps:
15
About this space The house has five bedrooms, each with its own private bathroom. A gourmet kitchen with a large dining ...
From $1368 per night (USD)
Expedia
From $696 per night (USD)
VRBO
Anne Hathaway, 8 bedrooms, 9 bathrooms, a commercial kitchen and dining room.
Bedrooms:
9
Bathrooms:
8
Sleeps:
14
About this space The Anne Hathaway House has seven bedrooms and seven and a half bathrooms, a huge commercial kitchen, ...
From $696 per night (USD)
VRBO
From $211 per night (USD)
Expedia
2 bedroom cabin plus loft, huge deck, lodge-style furnishings.
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Premium cabin, huge deck, lodge-style furnishings in an Alpine setting at 5200' elevation, just 18 miles east of downtow ...
From $211 per night (USD)
Expedia
From $636 per night (USD)
VRBO
Luxury condo with 2 bedrooms/2 bathrooms, sleeper sofa, full kitchen.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to Ashland's new luxury vacation destination located in the heart of downtown, just steps to the culinary deligh ...
From $636 per night (USD)
VRBO
From $1115 per night (USD)
Expedia
Pioneer Mega 3 vacation homes offering 8 Bedrooms, 5 bathrooms, laundry, TV, and kitchens.
Bedrooms:
5
Bathrooms:
8
Sleeps:
22
What this place offers : 8 Bedrooms, 5 bathrooms, laundry , Washing machine , Entertainment , TV , Heating an ...
From $1115 per night (USD)
Expedia
From $482 per night (USD)
VRBO
2-story, 3 bedroom modern home with king and queen beds, living room and kitchen.
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
About this space This two-story, modern home has three bedrooms. The primary bedroom has a king-sized bed and the guest ...
From $482 per night (USD)
VRBO
From $686 per night (USD)
Expedia
5 bedroom historic home with brand new furnishings, and is perfect for up to 14 guests.
Bedrooms:
3
Bathrooms:
5
Sleeps:
14
About this space This spacious five bedroom historic home has been fully renovated, has brand new furnishings, and is p ...
From $686 per night (USD)
Expedia
From $304 per night (USD)
VRBO
Spacious 2 bedroom historic home with two king beds and kitchenette.
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
About this space One block from OSF. Enjoy a relaxing getaway at the Pioneer House. originally built in 1904. Up to six ...
From $304 per night (USD)
VRBO
From $407 per night (USD)
Expedia
3 bedrooms include a king and two queen size beds, 2 bathrooms, and kitchenette.
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Historic home - One block from OSF. Easy access to dining, wine tasting, and shopping. Originally built in 1904, this ...
From $407 per night (USD)
Expedia
From $178 per night (USD)
VRBO
ABBOTT'S COTTAGES- Cardinal cottage. 1 bedroom/1 bath, short walk to downtown!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Enjoy breakfast with the hummingbirds on the redwood deck surrounded by wisteria and trumpet vines. This bright and chee ...
From $178 per night (USD)
VRBO
From $312 per night (USD)
VRBO
ABBOTT'S COTTAGES- The Bluejay. 3 bedroom/2 bath in walking distance to downtown
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
A beautiful 3 bedroom/2 bath house perfect for families and groups. Quiet, clean and comfortable. Just a 0.7 mile walk t ...
From $312 per night (USD)
VRBO
From $198 per night (USD)
VRBO
Ashland Urban Cabin - Centrally located & walking distance to SOU and Downtown
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Centrally located in the heart of Ashland, this cozy, thoughtfully updated retreat features 2 beautifully styled bedroom ...
From $198 per night (USD)
VRBO
From $100 per night (USD)
VRBO
Abbott's Cottages- The Wren. 1 bedroom within walking distance to downtown
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Located in Ashland's historic railroad district close to downtown Ashland, the Wren is a two-story, duplex unit with a s ...
From $100 per night (USD)
VRBO
From $110 per night (USD)
VRBO
Light-filled, upper story flat, walking distance to Oregon Shakespeare Festival
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
(Note: yes, the entire flat is yours. Your private entrance is completely separate from the downstairs flat. No adjoinin ...
From $110 per night (USD)
VRBO
From $262 per night (USD)
VRBO
Beautiful little place. Walk to town and theaters!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Nice things come in small packages! While this home is small it is delightfully eloquent. Sparkling clean with a moder ...
From $262 per night (USD)
VRBO
From $119 per night (USD)
VRBO
Nancy's Garden Cottage - 1. 5 Blocks to Downtown
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
We are located in the heart of Ashland. Only 1.5 blocks from Downtown. Enjoy the open Garden and Great location to all R ...
From $119 per night (USD)
VRBO
From $143 per night (USD)
VRBO
Monthly Rental Circular House blocks to Downtown & Oregon Shakespeare Festival
Bedrooms:
3
Bathrooms:
4
Sleeps:
6
A unique circular single-family house just blocks from Ashland's downtown dining & entertainment, Lithia Park, and the r ...
From $143 per night (USD)
VRBO
From $564 per night (USD)
VRBO
Indulgent Retreat: Pool, Hot Tub, Sauna
Bedrooms:
4
Bathrooms:
3
Sleeps:
10
Luxury 3BR escape with pool, and sauna awaits near the Oregon Shakespeare Festival. Indulge in refined living with 3 kin ...
From $564 per night (USD)
VRBO
From $530 per night (USD)
VRBO
Second Spring Property - 3 bedroom 2 bath luxury home in the heart of Ashland
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This luxury vacation rental is uniquely designed for elegance and comfort that will make you feel right at home. The new ...
From $530 per night (USD)
VRBO
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VRBO
Ashland Townhouse, furnished
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
3 bedroom, 2 and 1/2 bath furnished townhouse located 1/2 mile from grocery shopping and the YMCA, 1 mile from Southern ...
Click For Pricing
VRBO
From $269 per night (USD)
Expedia
Ashland's Mountain View Vacation Rental.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to Mountain View Cottage Ashland’s newest vacation rental The perfect place to stay for your next Ashland get a ...
From $269 per night (USD)
Expedia
From $252 per night (USD)
VRBO
Custom Ashland Home with Fantastic Mountain Views
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Beautiful 1360 square foot home on 2 acres. Modern, shed roof design with great windows and view of Grizzly Peak. Quiet ...
From $252 per night (USD)
VRBO
From $161 per night (USD)
Expedia
Beautiful Guest Suite with Private Deck Overlooking Forest and Waterfall
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This newly remodeled, modern guest suite is nestled in the Tolman Creek canyon and surrounded by a beautiful madrone, pi ...
From $161 per night (USD)
Expedia
From $133 per night (USD)
VRBO
Charming well appointed Cottage in Ashland ( 800 + sq. ft. )
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
The Farm Cottage is a renovated former horse hotel. It retains the charm of its former use yet is well appointed and upd ...
From $133 per night (USD)
VRBO
From $211 per night (USD)
Expedia
Chateau Herb ~ Juliet Carriage House Studio
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Welcome to the Carriage House Juliet at Chateau Herbe! A state-of-the art contemporary castle estate with stunning groun ...
From $211 per night (USD)
Expedia
From $233 per night (USD)
VRBO
Chateau Herbe ~ Rosalind Carriage House beautiful 1 bedroom Apartment
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
About the Space: This comfortable carriage house apartment is nestled in a gated castle community that boasts classical ...
From $233 per night (USD)
VRBO
From $241 per night (USD)
Expedia
Chateau Herb ~ Miranda Carriage House Apt
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Welcome to the Carriage House Miranda at Château Herbe, A contemporary retreat nestled within a one-of-a-kind castle est ...
From $241 per night (USD)
Expedia
From $165 per night (USD)
VRBO
Chateau Herbe ~ Vienna Room
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Wake up to breathtaking views of classical gardens and mountains beyond. This spacious private room has a private en sui ...
From $165 per night (USD)
VRBO
From $165 per night (USD)
Expedia
Chateau Herbe ~ Athens Room
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Wake up to breathtaking views of classical gardens and mountains beyond. This spacious private room has a private en sui ...
From $165 per night (USD)
Expedia
From $154 per night (USD)
VRBO
Florence Room at Chateau Herbe
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Relax in the window seat while taking in breathtaking views of classical gardens and mountains beyond. This private room ...
From $154 per night (USD)
VRBO
From $78 per night (USD)
Expedia
Beautiful New Studio in the Hills of Ashland
Bedrooms:
1
Bathrooms:
1
Sleeps:
1
Unwind in Ashland in this beautifully designed new studio. This cozy space is perfect for solo travelers looking for a p ...
From $78 per night (USD)
Expedia
From $180 per night (USD)
VRBO
Charming 2-bedroom house with WiFi, AC in peaceful Ashland
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Unwind in Ashland at this fabulous house. With 2 bedrooms including a queen bed and a twin bed, 2 bathrooms with showers ...
From $180 per night (USD)
VRBO
From $639 per night (USD)
Expedia
Hot tub | Sauna |Firepit |Sleeps 6!
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
This modern home features a brand-new hot tub, sauna, outdoor fire pit, grill, and an outdoor shower. Enjoy a gourmet ki ...
From $639 per night (USD)
Expedia
From $221 per night (USD)
VRBO
Chateau Herbe ~ Oberon Suite w/ Kitchen
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
This chateau apartment is nothing short of magical. Enjoy a tranquil environment with breathtaking views of the estate g ...
From $221 per night (USD)
VRBO
From $587 per night (USD)
Expedia
A Farmhouse Retreat
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
5 bedroom one story house located on this 10 acre country property, 10 minute drive to town. In a neighborhood of many ...
From $587 per night (USD)
Expedia
From $521 per night (USD)
VRBO
Asian Inspired Escape with View - Just 3 Miles from Downtown
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Asian meets Craftsman in this two story hillside home perched high above the city lights. Full kitchen with every ameni ...
From $521 per night (USD)
VRBO
From $390 per night (USD)
VRBO
The Best In Ashland: Magnificent View, Privacy, Quality, Convenience, Very Clean
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
3 bedroom, 2 bath villa on acreage within minutes of theaters, restaurants and shopping. Very private with modern kitche ...
From $390 per night (USD)
VRBO
From $183 per night (USD)
VRBO
Chateau Herbe - Shakespeare 1 Bedroom Suite w/ Kitchen
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Welcome to the Shakespeare Suite at Château Herbe A serene escape nestled within a modern-day castle estate Perched on ...
From $183 per night (USD)
VRBO
From $186 per night (USD)
VRBO
This Old Farmhouse. A few short minutes from town yet feels like sweet country.
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Welcome to our 1853 farmhouse—a step back in time with all the comforts of today. Relax and take in the bucolic views of ...
From $186 per night (USD)
VRBO
From $274 per night (USD)
VRBO
European Style Straw Bale Retreat
Bedrooms:
1
Bathrooms:
2
Sleeps:
8
Absorb the beauty of this European-style straw bale home located on 14 wooded acres in Ashland. Minutes from downtown, t ...
From $274 per night (USD)
VRBO
$Historic Dunn Ranch Ashland Oregon. Sleeps 12 to 14 Great for large groups.\n$
From $827 per night (USD)
Expedia
Historic Dunn Ranch Ashland Oregon. Sleeps 12 to 14 Great for large groups.\n
Bedrooms:
3
Bathrooms:
5
Sleeps:
14
Driving through the front gates you will find this Gorgeous and Stunning, completely refurbished, updated farmhouse orig ...
From $827 per night (USD)
Expedia
From $1078 per night (USD)
VRBO
Luxury Ashland Mountain Escape: Pool, Hot Tub
Bedrooms:
4
Bathrooms:
4
Sleeps:
12
Summary: Live the Southern Oregon paradise life at the Jefferson Estate — a fabulously appointed home on 8 acres, perfec ...
From $1078 per night (USD)
VRBO
From $768 per night (USD)
Expedia
Come stay at our farmhouse! A place to integrate all the beauty surrounding you!
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Our family ranch home is nestled at the base of Grizzly Peak, with expansive views of Mt Ashland, and the Rogue Valley. ...
From $768 per night (USD)
Expedia
From $179 per night (USD)
VRBO
Peaceful, spacious home on 8 acres. Pet-friendly, close to town, and a creek!
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
You will be an easy 10 minute drive from Downtown Ashland and feel like you are out in the country. The home is 1200 squ ...
From $179 per night (USD)
VRBO
From $721 per night (USD)
Expedia
Modern Farmhouse on Emigrant Creek. Peaceful, views, and a dance studio!
Bedrooms:
4
Bathrooms:
3
Sleeps:
8
Enjoy peace indoors and out in this spacious, stunning and serene home. It was built by a renowned local contractor in 2 ...
From $721 per night (USD)
Expedia

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Results: 174 Rentals