Book 5 Star Hotels in Winchester

Start date: Check-in selected.
To Date
End date: Check-out

Earn Orbucks instantly: $1 Orbuck = $1 USD, good toward hotels

Save 10% or more on select hotels with Insider Prices

Book on the app to instantly earn 5% on 350,000+ hotels

Oct 11 - Oct 12
Tonight
Check prices in Winchester for tonight, Oct 11 - Oct 12
Oct 12 - Oct 13
Tomorrow night
Check prices in Winchester for tomorrow night, Oct 12 - Oct 13

Featured Winchester 5 Stars Hotels

Avon Old Farms Hotel

Avon Old Farms Hotel

3.5 out of 5
279 Avon Mountain Rd, Avon, CT
Free Cancellation
Reserve now, pay when you stay
17.58 mi from city center
$158 nightly
The price is $182 total per night
$182 total
Oct 12 - Oct 13
Total with taxes and fees
At Avon Old Farms Hotel, guests enjoy features like an outdoor pool, a 24-hour gym, and a sauna. You'll find RV, bus, and truck parking. The front desk is staffed 24/7 to help with luggage storage, dry cleaning/laundry, and securing valuables. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Other amenities at this family-friendly hotel include free WiFi in public areas, conference space, and a business center.
Pool
Breakfast included
The Farmington Inn & Suites

The Farmington Inn & Suites

3 out of 5
827 Farmington Ave, Farmington, CT
Free Cancellation
Reserve now, pay when you stay
20.58 mi from city center
$164 nightly
The price is $189 total per night
$189 total
Oct 12 - Oct 13
Total with taxes and fees
The Farmington Inn & Suites offers a gym, meeting rooms, and a 24-hour business center. Multilingual staff at the front desk are standing by 24/7 to help with securing valuables, dry cleaning/laundry, and tours or tickets. Additional amenities include coffee/tea in a common area, a computer station, and express check-out.
Breakfast included
Pet friendly
Homewood Suites by Hilton Hartford-Farmington

Homewood Suites by Hilton Hartford-Farmington

3 out of 5
2 Farm Glen Blvd, Farmington, CT
Free Cancellation
Reserve now, pay when you stay
21.42 mi from city center
$140 nightly
The price is $161 total per night
$161 total
Nov 2 - Nov 3
Total with taxes and fees
At Homewood Suites by Hilton Hartford-Farmington, guests enjoy an indoor pool, a gym, and free WiFi in public areas. You can take advantage of free parking, along with a free area shuttle. The front desk has multilingual staff on hand 24/7 to help with securing valuables, luggage storage, and dry cleaning/laundry. Additional amenities include conference space, a 24-hour business center, and coffee/tea in a common area.
Pool
Breakfast included
Hampton Inn & Suites Hartford/Farmington

Hampton Inn & Suites Hartford/Farmington

2.5 out of 5
301 Colt Hwy, Farmington, CT
Free Cancellation
Reserve now, pay when you stay
21.91 mi from city center
$121 nightly
The price is $140 total per night
$140 total
Nov 10 - Nov 11
Total with taxes and fees
Guests staying at Hampton Inn & Suites Hartford/Farmington enjoy an indoor pool, a 24-hour gym, and free WiFi in public areas. There's free parking and a free area shuttle. Multilingual staff at the 24-hour front desk can assist with dry cleaning/laundry, luggage storage, and securing valuables. Additional amenities include a hot tub, conference space, and coffee/tea in a common area.
Pool
Hot Tub
DoubleTree by Hilton Hotel Bristol, Connecticut

DoubleTree by Hilton Hotel Bristol, Connecticut

4 out of 5
42 Century Dr, Bristol, CT
Free Cancellation
Reserve now, pay when you stay
22.04 mi from city center
$156 nightly
The price is $180 total per night
$180 total
Nov 2 - Nov 3
Total with taxes and fees
At DoubleTree by Hilton Hotel Bristol, Connecticut, guests enjoy an indoor pool, a 24-hour gym, and free WiFi in public areas. If you drive, put free valet parking to good use. The 24-hour front desk has multilingual staff ready to assist with concierge services, dry cleaning/laundry, and luggage storage. Additional amenities include a hot tub, conference space, and a 24-hour business center.
Pool
Hot Tub
Sheraton Hartford Hotel at Bradley Airport

Sheraton Hartford Hotel at Bradley Airport

3.5 out of 5
1 Bradley International Airport, Windsor Locks, CT
Free Cancellation
Reserve now, pay when you stay
21.87 mi from city center
$259 nightly
The price is $298 total per night
$298 total
Nov 1 - Nov 2
Total with taxes and fees
Guests of Sheraton Hartford Hotel at Bradley Airport enjoy a 24-hour gym, free WiFi in public areas, and conference space. Self parking is available for USD 19 per night. The front desk is staffed 24/7 to help with luggage storage, concierge services, and dry cleaning/laundry. Additional amenities include a 24-hour business center, a computer station, and a ballroom.
Pet friendly
Free WiFi
Extended Stay America Suites Hartford Farmington

Extended Stay America Suites Hartford Farmington

2.5 out of 5
1 Batterson Park Rd, Farmington, CT
Free Cancellation
Reserve now, pay when you stay
22.56 mi from city center
$102 nightly
The price is $117 total per night
$117 total
Nov 2 - Nov 3
Total with taxes and fees
Renovated in 2025, Extended Stay America Suites Hartford Farmington offers free WiFi in public areas, coffee in a common area, and laundry facilities. Free parking is available if you drive. The 24-hour front desk has staff standing by to help secure valuables, and answer any questions about the accommodations. This smoke-free hotel also has a vending machine.
Breakfast included
Pet friendly
Delamar West Hartford

Delamar West Hartford

4 out of 5
1 Memorial Road, West Hartford, CT
22.67 mi from city center
$360 nightly
The price is $412 total per night
$412 total
Nov 2 - Nov 3
Total with taxes and fees
Guests staying at Delamar West Hartford enjoy access to a full-service spa, a 24-hour gym, and free WiFi in public areas. If you decide to drive, there's free valet parking. The 24-hour front desk has multilingual staff ready to assist with luggage storage, concierge services, and dry cleaning/laundry. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Other amenities at this spa hotel include meeting rooms, a conference center, and a 24-hour business center.
Spa
Pet friendly
Fairfield Inn & Suites by Marriott Plainville

Fairfield Inn & Suites by Marriott Plainville

2.5 out of 5
400 New Britain Ave, Plainville, CT
Free Cancellation
Reserve now, pay when you stay
23.01 mi from city center
$101 nightly
The price is $116 total per night
$116 total
Nov 2 - Nov 3
Total with taxes and fees
At Fairfield Inn & Suites by Marriott Plainville, guests enjoy features like an indoor pool, a 24-hour gym, and free WiFi in public areas. There's free parking if you drive. The front desk is staffed 24 hours a day to help with dry cleaning/laundry and securing valuables. Additional amenities include conference space, a 24-hour business center, and coffee/tea in a common area.
Pool
Breakfast included
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.

Best 5 star hotels in Winchester

Guarantee yourself a relaxing time when you book the best of the best: 5 star hotels in Winchester. After all, treating yourself to the finer things is what vacations are about. 

What are the criteria for a 5 star hotel?
5 star hotel requirements include distinctive services and amenities that surpass all others. These Winchester hotels bring an incomparable degree of quality and attention to detail, with guest satisfaction being top priority. Your 5 star hotel should be dressed to impress, with design details like marble surfaces and hi-tech fixtures.

What amenities can I expect at a 5 star hotel?
Winchester 5 star hotels and resorts typically offer luxury amenities such as:

  • Gourmet restaurant
  • Full-service fitness center with pool
  • Luxury spa 
  • Welcome gifts upon arrival
  • Top-of-the-line beds and linens 
  • Designer personal care products
  • Premium cable, free Wi-Fi and device docking stations

How do I find an amazing 5 star hotel?
Finding 5 star hotel deals in Winchester with Orbitz is as easy as your stay will be. For the top-shelf vacation you deserve, we’ll help you choose the right hotel in the right place: 

  • Search hotels by price, ranging from $116 to $412
  • Find the best-loved hotels through word-of-mouth advice when you check out over reviews by Orbitz travelers
  • Choose from 668 5 star hotels in Winchester!

Winchester hotels essential information

Accommodation
668 hotels
Lowest Price
$116
Highest Price
$412
Popular hotels
Extended Stay America Suites Hartford Farmington, The Farmington Inn & Suites, Sheraton Hartford Hotel at Bradley Airport, Avon Old Farms Hotel, Hampton Inn & Suites Hartford/Farmington, Delamar West Hartford, Homewood Suites by Hilton Hartford-Farmington, Fairfield Inn & Suites by Marriott Plainville, DoubleTree by Hilton Hotel Bristol, Connecticut

Recent Reviews

Avon Old Farms Hotel

Avon Old Farms Hotel

5/5 Excellent
"Breakfast was really good. They have great espresso machines "
A verified traveler stayed at Avon Old Farms Hotel
Posted 2 days ago
Avon Old Farms Hotel

More to Explore