Winchester Vacations

Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*

Choose two or more items and save on your trip:

Top Hotel Deals

Riverfront Inn Roseburg

Riverfront Inn Roseburg

2 out of 5
315 W Harvard Ave, Roseburg, OR
7.48 km from city center
Stay at this motel in Roseburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...
Motel 6 Sutherlin, OR

Motel 6 Sutherlin, OR

2 out of 5
1400 Hospitality Way, Sutherlin, OR
11.74 km from city center
Stay at this motel in Sutherlin. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. ...
Holiday Inn Express Roseburg by IHG

Holiday Inn Express Roseburg by IHG

2.5 out of 5
375 Harvard Blvd, Roseburg, OR
7.48 km from city center
Book a stay at this business-friendly hotel in Roseburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Super 8 by Wyndham Roseburg

Super 8 by Wyndham Roseburg

2.5 out of 5
3200 Nw Aviation Dr I-5 Exit # 127, Roseburg, OR
3.57 km from city center
Book a stay at this business-friendly hotel in Roseburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Motel 6 Roseburg, OR

Motel 6 Roseburg, OR

2 out of 5
3100 Nw Aviation Dr, Roseburg, OR
3.53 km from city center
Stay at this motel in Roseburg. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. ...
Best Western Garden Villa Inn

Best Western Garden Villa Inn

2.5 out of 5
760 NW Garden Valley Boulevard, Roseburg, OR
5.83 km from city center
Book a stay at this business-friendly hotel in Roseburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Sleep Inn & Suites Roseburg North Near Medical Center

Sleep Inn & Suites Roseburg North Near Medical Center

2.5 out of 5
2855 NW Edenbower Blvd, Roseburg, OR
4.03 km from city center
Book a stay at this business-friendly hotel in Roseburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Rosewood Inn and Suites

Rosewood Inn and Suites

2.5 out of 5
790 NW Garden Valley Blvd, Roseburg, OR
5.46 km from city center
Stay at this motel in Roseburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Umpqua ...
Best Western Plus Hartford Lodge

Best Western Plus Hartford Lodge

2.5 out of 5
150 Myrtle St, Sutherlin, OR
12.13 km from city center
Book a stay at this business-friendly hotel in Sutherlin. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Comfort Inn Roseburg

Comfort Inn Roseburg

2.5 out of 5
1539 NW Mullholland Drive, Roseburg, OR
5.74 km from city center
Book a stay at this golf hotel in Roseburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. ...
Hampton Inn & Suites Roseburg

Hampton Inn & Suites Roseburg

2.5 out of 5
1620 Nw Mulholland Dr, Roseburg, OR
5.63 km from city center
Stay at this hotel in Roseburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...
Rice Hill Inn

Rice Hill Inn

2 out of 5
621 John Long Rd, Oakland, OR
29.11 km from city center
Stay at this motel in Oakland. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attraction ...
Quality Inn Central Roseburg

Quality Inn Central Roseburg

2.5 out of 5
427 Nw Garden Valley Blvd, Roseburg, OR
5.89 km from city center
Book a stay at this business-friendly hotel in Roseburg. Enjoy free breakfast, free parking, and an outdoor pool. Our guests praise the breakfast and the helpful ...
Umpqua Valley Hotel

Umpqua Valley Hotel

2.5 out of 5
610 W Madrone St, Exit off 124, Roseburg, OR
7.36 km from city center
Book a stay at this business-friendly hotel in Roseburg. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Stewart Park and Umpqua Valley ...
Howard Johnson by Wyndham Roseburg

Howard Johnson by Wyndham Roseburg

2 out of 5
978 NE Stephens St, Garden Valley Blvd / Stephens, Roseburg, OR
6.6 km from city center
Stay at this motel in Roseburg. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions ...
Don't see what you're looking for?
See all available properties in Winchester
View all properties
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Top Flight Deals

These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Hawaiian Airlines
Tue, Jan 13 - Mon, Jan 19
LAS
Harry Reid Intl.
EUG
Eugene
$205 Roundtrip, found 4 days ago
$205
Roundtrip
found 4 days ago
Select Hawaiian Airlines flight, departing Tue, Jan 13 from Harry Reid Intl. to Eugene, returning Mon, Jan 19, priced at $205 found 4 days ago
Delta
Mon, Jan 12 - Mon, Jan 19
LAS
Harry Reid Intl.
EUG
Eugene
$209 Roundtrip, found 4 days ago
$209
Roundtrip
found 4 days ago
Select Delta flight, departing Mon, Jan 12 from Harry Reid Intl. to Eugene, returning Mon, Jan 19, priced at $209 found 4 days ago
United
Mon, Jan 12 - Sun, Jan 18
LAS
Harry Reid Intl.
EUG
Eugene
$209 Roundtrip, found 4 days ago
$209
Roundtrip
found 4 days ago
Select United flight, departing Mon, Jan 12 from Harry Reid Intl. to Eugene, returning Sun, Jan 18, priced at $209 found 4 days ago
Alaska Airlines
Mon, Jan 12 - Sun, Jan 18
LAS
Harry Reid Intl.
EUG
Eugene
$221 Roundtrip, found 4 days ago
$221
Roundtrip
found 4 days ago
Select Alaska Airlines flight, departing Mon, Jan 12 from Harry Reid Intl. to Eugene, returning Sun, Jan 18, priced at $221 found 4 days ago
American Airlines
Mon, Jan 12 - Sun, Jan 18
LAS
Harry Reid Intl.
EUG
Eugene
$254 Roundtrip, found 4 days ago
$254
Roundtrip
found 4 days ago
Select American Airlines flight, departing Mon, Jan 12 from Harry Reid Intl. to Eugene, returning Sun, Jan 18, priced at $254 found 4 days ago