Best Cottages in Jacksonville in 2026

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Our top choices for Jacksonville cottages

A two-story house with a front porch, a covered entryway, and a small front yard.

1. Charming Jacksonville cottage with a front porch, full kitchen, off-street parking, and walkable access to Britt Festival, downtown shops, restaurants, and wine tasting. Features two bedrooms, two bathrooms, and peaceful historic charm.

Jacksonville Historic District

Richard

includes taxes & fees

31 Aug - 1 Sept

A house with a covered porch, a door, a bench, and a chair.

2. Charming Jacksonville Studio with AC • Easy Walk to Town & Britt Festival

Jacksonville, OR

Kimberley C.

includes taxes & fees

21 Sept - 22 Sept

A small, single-story house with a white picket fence, a purple front door, and a porch with white railings.

3. Historic Bradshaw House!

Jacksonville

Linda J.

includes taxes & fees

30 Aug - 31 Aug

A bedroom with a fireplace, a bed with a headboard, a window, and a wall-mounted picture.

4. Walk to the Britt Festival and downtown Jacksonville from this newly remodeled luxury cottage. Features a king bed with luxury linens, dramatic centerpiece fireplace, pull-out sofa, full kitchen, and spa-style bathroom.

Jacksonville

Christopher

includes taxes & fees

30 Aug - 31 Aug

A residential property with a paved driveway leading to a front door, a wooden fence, and a small garden area.

5. The Williams - luxe 2-bedroom cottage w/onsite parking in downtown Jacksonville

Jacksonville Historic District

darren t.

includes taxes & fees

7 Sept - 8 Sept

A house with a window, a wooden fence, and a sign reading '160 C Street'.

6. Fireside Cottage in Downtown Jacksonville

Jacksonville Historic District

includes taxes & fees

1 Sept - 2 Sept

A small house with a porch, a bench, and a tree with white blossoms.

7. Cozy Cottage on Applegate River Micro-Farm at Vineyards.15 Min to Jacksonville

Jacksonville

Nikki F.

includes taxes & fees

7 Sept - 8 Sept

A blue house with a patio, a small table and chairs, and a hanging flower basket.

8. Charming Cottage near historic Jacksonville. Wi-Fi, fenced pet area.

Central Point

Katie B.

includes taxes & fees

31 Aug - 1 Sept

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Top Jacksonville Hotel Reviews

Wine Country Inn

10/10 Excellent

"Great location and hotel accommodations. Have stayed here many times and am always pleased with it."

Compass by Margaritaville in Medford

10/10 Excellent

"I needed a hotel for one night on a road trip and randomly found this property. It was absolutely bizarre to feel like you were in the Florida Keys on a tropical vacation when you were in fact in Medford, OR., but I was not angry about it. The pool was fantastic, the bar/restaurant service was top-notch (and also delicious), and the rooms were well done. My only issue was the bed -- very, very firm -- I ended up having to take advil overnight bc my back hurt. Though, that's just a personal preference, so don't let it be the reason you don't stay here! If I'm passing through again, I'd definitely stay here!"

Best Western Windsor Inn

10/10 Excellent

"Our first stay. We found the property well-located for activities in downtown Ashland with adequate safe parking. The staff was available without being intrusive. Ryan was particularly helpful. Our room was quiet, clean and furnished as advertised, no surprises. One of the most organized and comfortable (included) breakfast options we've had– simple, but with a nice range of options and, again, clean. The grounds are well-maintained and there is easy on/off I-5 access. (one note: the property has no elevator, so if this is a concern, would recommend contacting the desk in advance for assistance in planning)"

Executive Residency by Best Western Medford

10/10 Excellent

"Our stay was fine for staying 1 night before a flight. The room was nice (freezing when we arrived, however) because we always appreciate an extra seat or sofa in our rooms and the small kitchenette was great-with a full size fridge. They weren't offering any type of breakfast at this point but I think it's coming since taking over as a Best Western affiliated hotel."

Find out more about Jacksonville

Jacksonville Cottages information

Number of reviews	842
Accommodation	129 Cottages
Lowest Price	£134
Highest Price	£316

Frequently asked questions

How much do cottages in Jacksonville cost?

Expect to pay between £134 and £316 per night for cottages in Jacksonville. No matter your budget, a fantastic stay is only a click or two away on Expedia. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.

What are the best cottages in Jacksonville?

Choose from multiple cottages in Jacksonville that have a total average guest review rating of 9.7. Wine Suite At Rellik House. Winery And Alpaca Farm is a great place to put your feet up between adventures. This 3.5-star cottage also comes with a firepit and a vineyard. Rellik House. Winery And Alpaca Farm is another leading pick with travellers visiting this area. It has a 3.5-star rating and amenities including an attached winery and a vineyard.

How many cottages are there in Jacksonville?

Choose from 129 cottages in Jacksonville. No matter if you're holidaying with the family or organising a weekend retreat with close friends, Expedia can help you find the ideal space to escape the hustle and bustle.

Are there any family-friendly cottages in Jacksonville?

Settle in at Wine Suite At Rellik House. Winery And Alpaca Farm, a 3.5-star cottage just a short drive from town. Conveniences here include a firepit and WiFi. Another family-friendly pick where you can swap the concrete jungle for nature is Rellik House. Winery And Alpaca Farm. WiFi and clothes washing facilities help make this 3.5-star cottage a favourite among guests. Once you've checked in and unpacked your suitcase, there are loads of family-friendly attractions to visit in and around Jacksonville. Beekman Loop Trail and Sarah Zigler Interpretive Trail are two of our top picks.

Why book your cottage in Jacksonville with Expedia?

We think that holidays should be simple, so if you're chasing cottages in Jacksonville at a competitive price, Expedia has your back. Save those pennies and opt for a thrifty option far from the hustle and bustle, or splurge on an upscale cottage to pamper your favourite people.

How can I find cheap cottages in Jacksonville?

A wonderful way to uncover cheap cottages in Jacksonville is with Expedia's filter tool. Refine your search by budget, star rating and amenities to nab unbeatable bargains in a few clicks.

What is there to do in Jacksonville near my cottage?

Whatever you love doing, Jacksonville has loads to capture your imagination. Sarah Zigler Interpretive Trail, Beekman Loop Trail and Britt Pavilion are on many visitors' lists. You shouldn't miss Red Lily Vineyards, Jacksonville Cemetery and Ruch Library either. With Expedia's hotel deals in Jacksonville, you can see more renowned attractions like these with the cash you save.

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Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Jacksonville cottages

1. Charming Jacksonville cottage with a front porch, full kitchen, off-street parking, and walkable access to Britt Festival, downtown shops, restaurants, and wine tasting. Features two bedrooms, two bathrooms, and peaceful historic charm.

2. Charming Jacksonville Studio with AC • Easy Walk to Town & Britt Festival

3. Historic Bradshaw House!

4. Walk to the Britt Festival and downtown Jacksonville from this newly remodeled luxury cottage. Features a king bed with luxury linens, dramatic centerpiece fireplace, pull-out sofa, full kitchen, and spa-style bathroom.

5. The Williams - luxe 2-bedroom cottage w/onsite parking in downtown Jacksonville

6. Fireside Cottage in Downtown Jacksonville

7. Cozy Cottage on Applegate River Micro-Farm at Vineyards.15 Min to Jacksonville

8. Charming Cottage near historic Jacksonville. Wi-Fi, fenced pet area.

9. Peaceful Countryside Stay with Scenic Views- 5 minutes to Jacksonville

10. Pet Friendly, Light-filled, Organic Studio, Full Kitchen, Hot Tub

11. Downtown Mint

12. Wake to breathtaking sunrises over the rolling hills! Relax by the fire under the stars, & sunset dinners beneath fragrant wisteria pergola. Surrounded by wineries and minutes from historic Jacksonville. Charm, convenience & budget friendly.

13. Rosewood Studio | Private Cottage Near Downtown

14. HOLLY HOUSE ~ Organic, Dog-friendly Garden Cottage

15. Paschal Winery

16. Charming 2 BR riverside stopover in Gold Hill. Private hot tub, river access, and just down the road from Del Rio Vineyards. Perfect base for exploring the Rogue Valley. Pet-friendly!

17. The Vintage Cottage with riverfront access

18. Modern cottage centrally located with private access to the Rogue River!

19. Charming carriage house in Ashland near downtown

20. The Ashland Cottage, walk to town

Find holiday rentals that suit your style

Top Jacksonville Hotel Reviews

Wine Country Inn

Find out more about Jacksonville

Jacksonville Cottages information

Frequently asked questions

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