Search for Cheap Deals on
Hotels in Winchester

Photo by Donny Campos

Choose from 403 Winchester Hotel Deals

The Colonial Hotel
The Colonial Hotel
3 out of 5
625 Betty Spring Road, Gardner, MA
  • 50 min drive from Pisgah State Park
The price is $156 per night from Jan 8 to Jan 9
$156
includes taxes & fees
Jan 8 - Jan 9
Stay at this 3-star business-friendly hotel in Gardner. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the restaurant and the helpful ...
8.4/10 Very Good! (1,003 reviews)
"Gorgeous property"

Reviewed on Jan 4, 2025

The Colonial Hotel
Colonial Motel And Spa
Colonial Motel And Spa
3 out of 5
889 Putney Rd, Brattleboro, VT
  • 11 min drive from Pisgah State Park
The price is $108 per night from Jan 8 to Jan 9
$108
includes taxes & fees
Jan 8 - Jan 9
Stay at this 3-star spa motel in Brattleboro. Enjoy free WiFi, free parking, and 2 indoor pools. Our guests praise the helpful staff and the clean rooms in our ...
6.6/10 (1,001 reviews)
"Like size of room"

Reviewed on Dec 8, 2024

Colonial Motel And Spa
Hampton Inn Brattleboro
Hampton Inn Brattleboro
2.5 out of 5
1378 Putney Road, Brattleboro, VT
  • 12 min drive from Pisgah State Park
The price is $110 per night from Jan 14 to Jan 15
$110
includes taxes & fees
Jan 14 - Jan 15
Book a stay at this business-friendly hotel in Brattleboro. Enjoy free breakfast, free parking, and a fitness center. Our guests praise the breakfast and the ...
8.2/10 Very Good! (1,003 reviews)
"The hotel was clean and staff were helpful. The breakfast was better than average and they have 24 hours hot coffee and tea. The pool and hot tub were closed which was a disappointment. A pipe burst in our bathroom in the middle of the night, but the staff were quick to get us a new room and were ..."

Reviewed on Jan 4, 2025

Hampton Inn Brattleboro
Comfort Inn & Suites Brattleboro I-91
Comfort Inn & Suites Brattleboro I-91
2.5 out of 5
1186 Putney Road, Brattleboro, VT
  • 12 min drive from Pisgah State Park
The price is $114 per night from Jan 12 to Jan 13
$114
includes taxes & fees
Jan 12 - Jan 13
Book a stay at this business-friendly hotel in Brattleboro. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
8.6/10 Excellent! (547 reviews)
"Price and quality makes it great"

Reviewed on Jan 3, 2025

Comfort Inn & Suites Brattleboro I-91
Days Inn by Wyndham Keene NH
Days Inn by Wyndham Keene NH
2 out of 5
3 Ash Brook Road, Keene, NH
  • 17 min drive from Pisgah State Park
The price is $98 per night from Jan 16 to Jan 17
$98
includes taxes & fees
Jan 16 - Jan 17
Book a stay at this business-friendly hotel in Keene. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
7.2/10 Good! (976 reviews)
"Clean comfy room:)"

Reviewed on Jan 5, 2025

Days Inn by Wyndham Keene NH
Courtyard by Marriott Keene Downtown
Courtyard by Marriott Keene Downtown
3 out of 5
75 Railroad St, Keene, NH
  • 20 min drive from Pisgah State Park
The price is $165 per night from Jan 12 to Jan 13
$165
includes taxes & fees
Jan 12 - Jan 13
Stay at this 3-star business-friendly hotel in Keene. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
8.6/10 Excellent! (1,003 reviews)
"Lovely staff"

Reviewed on Dec 16, 2024

Courtyard by Marriott Keene Downtown
The Putney Inn
The Putney Inn
2.5 out of 5
57 Putney Landing Rd, Putney, VT
  • 22 min drive from Pisgah State Park
The price is $102 per night from Jan 9 to Jan 10
$102
includes taxes & fees
Jan 9 - Jan 10
Book a stay at this business-friendly motel in Putney. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms ...
8.2/10 Very Good! (1,002 reviews)
"The check in staff was very friendly. We arrived late in the evening. Room was clean and quiet. It was a last minute stay before heading to a ski hill. It worked out well for the price."

Reviewed on Jan 4, 2025

The Putney Inn
The Covered Bridge Inn
The Covered Bridge Inn
2.5 out of 5
1043 Putney Road, Brattleboro, VT
  • 11 min drive from Pisgah State Park
The price is $187 per night from Jan 8 to Jan 9
$187
includes taxes & fees
Jan 8 - Jan 9
Book a stay at this business-friendly hotel in Brattleboro. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
8/10 Very Good! (1,001 reviews)
"Everything is right there I mean literally everything was right there"

Reviewed on Dec 14, 2024

The Covered Bridge Inn
Latchis Hotel
Latchis Hotel
2.5 out of 5
50 Main Street, Brattleboro, VT
  • 9 min drive from Pisgah State Park
The price is $131 per night from Jan 8 to Jan 9
$131
includes taxes & fees
Jan 8 - Jan 9
Stay at this hotel in Brattleboro. Enjoy free WiFi, free parking, and conference space. Our guests praise the helpful staff and the clean rooms in our reviews. ...
8.4/10 Very Good! (688 reviews)
"Very cool place. Super retro. Loved the record players and records everywhere. And it smells like popcorn, always."

Reviewed on Dec 29, 2024

Latchis Hotel
Hampton Inn & Suites Keene
Hampton Inn & Suites Keene
2.5 out of 5
126 Key Rd, Keene, NH
  • 18 min drive from Pisgah State Park
The price is $147 per night from Jan 26 to Jan 27
$147
includes taxes & fees
Jan 26 - Jan 27
Book a stay at this business-friendly hotel in Keene. Enjoy free parking, room service, and a 24-hour fitness center. Our guests praise the breakfast and the ...
8.8/10 Excellent! (273 reviews)
"Nice simple and modern. Great customer service. Check in and out was simple and quick. Unfortunately pool wasnt open but guests where advised the Best Western across the way was allowing their guests to show room cards to be able to use the pool their facility. Clean rooms but no laundry amenities ..."

Reviewed on Jan 1, 2025

Hampton Inn & Suites Keene
Hampton Inn & Suites Greenfield
Hampton Inn & Suites Greenfield
2.5 out of 5
184 Shelburne Rd, Greenfield, MA
  • 43 min drive from Pisgah State Park
The price is $151 per night from Jan 26 to Jan 27
$151
includes taxes & fees
Jan 26 - Jan 27
Book a stay at this business-friendly hotel in Greenfield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
8.6/10 Excellent! (766 reviews)
"The property was very clean, comfortable, and the room was clean and nice. The only complaint I have is it was very noisy with other guests being next to us and above us. We could hear their tv at later times at night and the people above us were walking around at 1am. Not necessarily anything the ..."

Reviewed on Dec 24, 2024

Hampton Inn & Suites Greenfield
Holiday Inn Express Hotel & Suites Brattleboro, an IHG Hotel
Holiday Inn Express Hotel & Suites Brattleboro, an IHG Hotel
2.5 out of 5
100 Chickering Drive, Brattleboro, VT
  • 11 min drive from Pisgah State Park
The price is $154 per night from Feb 3 to Feb 4
$154
includes taxes & fees
Feb 3 - Feb 4
Book a stay at this business-friendly hotel in Brattleboro. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
8.6/10 Excellent! (953 reviews)
"Place is clean, safe, well lit, plenty of parking, friendly and helpful staff, and breakfast is included. Would stay again, highly recommend."

Reviewed on Dec 28, 2024

Holiday Inn Express Hotel & Suites Brattleboro, an IHG Hotel
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.

Find cheap hotels in Winchester

You’re not an average traveler—and Hotwire knows it. Your wanderlust takes you off the beaten path to discover unique adventures and every travel destination’s lesser-known tourist scenes. Hotwire has the hookup! Book your Winchester hotel with Hotwire to complete your one-of-a-kind travel checklist.

For you, intrepid voyager, Hotwire has a large selection of the best hotels in Winchester.

Choosing the right hotel in New Hampshire has everything to do with the way you want your trip to go. If you’ve scribbled a few obscure destinations on your itinerary, you probably already have a good sense of how your getaway is taking shape. Lean into that by booking one of Winchester’s 403 hotels. Choose the one that best catches your trip’s tourist drift.

If you’re traveling during the week for business, Hotwire can score you a luxury hotel for as low as $98. In town for pleasure? Hotwire still has you covered. If you’re in the mood for a quick last-minute weekend getaway or spa retreat, you can get great Winchester hotel deals at the last minute.

While traveling, where you stay plays a major role in your overall vacation enjoyment. Choosing the right hotel is just as important as making sure you book the right flight and car rental. If you’re traveling with family or friends, you may need to book a hotel with connecting rooms. If you enjoy an elegant and relaxing hotel ambiance, opt for one of Hotwire’s luxury hotels in Winchester. No matter your reason for visiting Winchester, with Hotwire’s large selection of hotels in the area, you’re sure to book a hotel that meets all your accommodation needs.

Frequently Asked Questions About Winchester hotels

Where can I find the best last-minute travel deals?

If you’re traveling in the spirit of spontaneity, you’ll love the idea of leaving your exact hotel choice up to chance. With Hotwire Hot Rates, you can unlock great deals on your next flight, hotel, or car rental. Just plug in your general preferences and let Hotwire choose last-minute hotel deals in Winchester for as low as $98.

How many hotels are there in Winchester?

With over 403 hotels in Winchester, you’re sure to find one that best matches your travel mood. When you book with Hotwire, you can score a stellar home away from home for as low as $98.

How to find cheap car rentals in Winchester?

Finding a cheap car rental deal in Winchester is as easy as scoring cheap hotels in Winchester. Hotwire partners with top-of-the-line car rental companies to bring you a large selection of affordable options. Whether you’re in need of a large SUV for the entire family or a more compact but stylish vehicle, Hotwire has you covered. You can unlock great car rental deals if you book a Hotwire Hot Rate at the last minute.