Holiday homes & B&B in Windsor
Choose the right place for you
REVIEWS
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9+ Exceptional
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8+ Fabulous
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7+ Very Good
Vacation rental deals in Windsor
We have selected the best vacation rentals in Windsor. Save money with Bluepillow by comparing the best deals from major travel websites in Windsor
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Windsor - United States
Private studio on serene urban farm
- 2 Guests 1Bedroom
10 Exceptional (328)Enjoy spectacular views of the Rogue Valley from this private studio apartment attached to main house, but with separate entrance. Your 119 square foot room includes full size bed, full bath, fridge, microwave, ...Check Availability -
Windsor - United States
Thankful Too
- 3 Guests 0Bedroom
10 Exceptional (80)Hobby Farm Setting in the hills outside of Medford, only a few miles but a world away. Peaceful beaucolic Setting, Mountain View’s, starry nights. Small varietal orchard, chickens and ducks. Nearby to ...Check Availability -
Windsor - United States
Private entry, queen BR + bathroom
- 2 Guests 1Bedroom
10 Exceptional (180)2.5 miles from Shakespeare in Ashland, big open mountain views from window and deck across landscaped yard, in the country, convenient parking, unobtrusive on-sight owner couple are your hosts. Private ...Check Availability -
Windsor - United States
1952 International METRO Bus Love
- 2 Guests 1Bedroom
10 Exceptional (328)Everyone falls in love with our 1952 International Metro Gypsy Wagon. It's cozy, delightful and colorful. This converted school bus fits two, with a shared kitchen in main house and a NEW, free-standing ...Check Availability -
Windsor - United States
Cozy camping close to town
- 2 Guests 0Bedroom
10 Exceptional (367)The 1973 Kit Companion is a 15-foot trailer converted to maximize space and guest experience. Featuring a water dispenser, coffee maker, tea kettle, lending library, and games; this adorable camper is ...Check Availability -
Windsor - United States
Long Shadow Fields - your organic farm retreat
- 2 Guests 1Bedroom
10 Exceptional (128)Enjoy a farm-stay surrounded by 4 acres of organic garden and pasture outside of Talent, Oregon. I offer a renovated guest room with a private entrance off the back patio. Amenities include a queen Sleep ...Check Availability
Save on Bed & Breakfast in Windsor
Are you looking for an accommodation in Windsor and do you want to save money? Choose from 45 Bed & Breakfasts in Windsor
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Windsor - United States
Winchester Inn
- Hotel
10 Exceptional (303)Winchester Inn is set in Ashland, 1.6 miles from Southern Oregon University Nat. Guests can enjoy the on-site bar. Each room at this hotel is air conditioned and features a flat-screen TV. Certain rooms ...Check Availability -
Windsor - United States
Innkeeper's Room
- Hotel
10 Exceptional (9)Guests stepping inside this boutique European-style hotel for the first time are greeted with a warm ambiance, personable front desk staff, plush reading areas, clawfoot tubs, period furnishings and original ...Check Availability -
Windsor - United States
Britt Cottage - Perfect Location!!
- Hotel
9.8 Exceptional (8)"We stayed at the Britt Cottage on the night of our wedding, and could not have been more pleased! The suite was impeccably clean and had everything we needed to be comfortable. We sat outside on the private ...Check Availability -
Windsor - United States
Sovana Inn
- Hotel
8.8 Fabulous (527)Offering an outdoor pool, Sovana Inn is located in Medford. Free WiFi access is available. Each air-conditioned room here is equipped with a microwave, a mini refrigerator, and a coffee machine. A satellite ...Check Availability -
Windsor - United States
Lori Lanes 'Juliet Cottage' ~ 2 Bedroom ~ Downtown
- Hotel
9 Exceptional (2)Completely renovated, and just five blocks from Downtown Ashland and the Oregon Shakespeare Festival! This cottage has two private bedrooms, with a queen bed in each. The bathroom has an oversize walk-in ...Check Availability -
Windsor - United States
Best Western Windsor Inn
- Hotel
9 Exceptional (1593)One of our top picks in Ashland.Offering English Tudor-style architecture, Best Western Windsor Inn is located in Ashland, Oregon. An outdoor swimming pool, a fitness centre, and free Wi-Fi access are ...Check Availability
Farmhouse or Hotel? Choose from the best offers
Choose the accommodation tailor-made for you for your next vacation: sleep in a farmhouse or sleep in a hotel?
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![Farmstays near Windsor]()
Farmstays near Windsor -
![Hotels near Windsor]()
Hotels near Windsor
The best places to stay in Windsor
Book an apartment in Windsor and choose the right accommodation for your needs
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Windsor - United States
Cozy/rural close to town 1
- 3 Guests 1Bedroom
10 Exceptional (422)This space is full of natural light and perfect for a quick overnight stay or longer Ashland visit. The home is located on the edge of town with horses and pasture across the street and stunning mountain ...Check Availability -
Windsor - United States
Susan's Garden Retreat - Private Room
- 2 Guests 1Bedroom
10 Exceptional (112)Enjoy yourself at my comfortable country retreat! Spread out in the large guestroom, explore the secluded garden with mature trees, pond, organic vegetable/herb garden or relax in the soaking bathtub. ...Check Availability -
Windsor - United States
The Green Arrow Loft
- 6 Guests 0Bedroom
10 Exceptional (213)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 ...Check Availability -
Windsor - United States
Carter Lane Cottage
- 4 Guests 1Bedroom
10 Exceptional (151)Welcome to the Carter Lane Cottage. Guests can retreat to this quiet oasis for total comfort and relaxation. Enjoy the spacious cottage, bike to nearby trails and pathways, or drive less than 9 minutes ...Check Availability -
Windsor - United States
1 BR Guest Suite
- 2 Guests 1Bedroom
10 Exceptional (341)1 bedroom, 1 bath suite, private entrance and living room, in quiet rural setting. About 20 minutes drive to both Ashland and Jacksonville. 1 mile from Medford Sports Park. The newly remodeled 1 bedroom ...Check Availability -
Windsor - United States
Oak Haven -Master Suite Bedroom
- 5 Guests 1Bedroom
10 Exceptional (165)Our home is a unique ranch style with laminated, curved, open beam ceilings & hardwood floors. The Master Suite features; a small kitchenette, a modest but full bathroom, and a spacious “L” shaped master ...Check Availability
