Deals on vacations and trips to Winchester

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Omni New Haven Hotel at Yale

Omni New Haven Hotel at Yale

4 out of 5
Downtown New Haven
Price was $638, price is now $514 per person
$514
per person
Jun 26 - Jun 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Self parking, a coffee shop, and limo/town car service are also offered.
Landing Apartments New Haven

Landing Apartments New Haven

3 out of 5
West New Haven
Price was $901, price is now $676 per person
$676
per person
Jul 15 - Jul 20
found 1 day ago
Roundtrip flight included
Fort Myers (RSW) to New Haven (HVN)
A gym, self parking, and barbecue grills are featured at this apartment. WiFi in public areas is free. A business center, a garden, and a picnic area are also on offer.
Madison Beach Hotel

Madison Beach Hotel

4 out of 5
Madison Center
Save 100% on your flight
Price was $2,552, price is now $1,926 per person
$1,926
per person
Jun 25 - Jun 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
This smoke-free hotel features a private beach, a full-service spa, and a restaurant. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Enjoy the gym and perks like free WiFi.
Landing Apartments New Haven Near Dixwell

Landing Apartments New Haven Near Dixwell

3 out of 5
Newhallville
Price was $849, price is now $664 per person
$664
per person
Jun 26 - Jun 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
This apartment includes free WiFi in public areas and a virtual front desk.
New Haven Hotel

New Haven Hotel

3.5 out of 5
Downtown New Haven
Price was $772, price is now $604 per person
$604
per person
Jun 26 - Jun 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
A gym, self parking, and laundry facilities are featured at this hotel. WiFi in public areas is free. Traveling on business? Take advantage of the 2 conference rooms, along with dry cleaning/laundry services.

Top Winchester hotels deals

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
$162 nightly
The price is $187 total per night
$187 total
Jun 1 - Jun 2
Total with taxes and fees
This hotel features a restaurant, a gym, and a bar/lounge. Business travelers can take advantage of the 24-hour business center. Enjoy the free continental breakfast each morning.
Breakfast included
Pet friendly
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
$254 nightly
The price is $292 total per night
$292 total
May 31 - Jun 1
Total with taxes and fees
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Self parking, a coffee shop, and a computer station are also offered.
Pet friendly
Free WiFi
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
$130 nightly
The price is $150 total per night
$150 total
Jun 4 - Jun 5
Total with taxes and fees
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the free WiFi in public areas and free internet in public areas. Enjoy the hot tub and free perks like on-the-go breakfast and free self parking.
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
$149 nightly
The price is $171 total per night
$171 total
May 28 - May 29
Total with taxes and fees
This hotel features an outdoor pool, a 24-hour gym, and a restaurant. Enjoy the seasonal outdoor pool and free perks like buffet breakfast and WiFi in public areas. You'll appreciate the sauna, bar/lounge, and wedding services.
Pool
Breakfast included
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
$151 nightly
The price is $174 total per night
$174 total
Jun 3 - Jun 4
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Enjoy the 24-hour gym and perks like free valet parking and free WiFi. Enjoy the hot tub and conveniences like a 24-hour front desk and laundry facilities.
Pool
Hot Tub
Delamar West Hartford

Delamar West Hartford

4 out of 5
1 Memorial Road West Hartford CT
Free Cancellation
Reserve now, pay when you stay
$334 nightly
The price is $382 total per night
$382 total
Jun 14 - Jun 15
Total with taxes and fees
A full-service spa, a 24-hour gym, and a restaurant are all featured at this smoke-free hotel. Relax with a drink at the bar/lounge and enjoy perks like free valet parking and free WiFi. Free self parking, a 24-hour business center, and a terrace are also offered.
Spa
Pet friendly
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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.

Popular places to visit

Highland Lake

Commune with nature and explore the great outdoors at Highland Lake during your travels in Winchester.

Highland Lake

Northwestern Connecticut Community College

Walk around the campus at Northwestern Connecticut Community College as part of your travels around Winchester.

Northwestern Connecticut Community College

Platt Hill State Park

You can take time to visit Platt Hill State Park during your travels to Winchester.

Platt Hill State Park

Frequently asked questions

How much are vacation packages to Winchester?
You'll be pleasantly surprised — you can unwind in Winchester for a mere $514. At Travelocity, we save you time and money with our awesome vacation package deals. With flights, hotels and experiences all ready to go at our one-stop shop, why wait?
Where can I get the best vacation package deals for Winchester?
For the best Winchester package deal, you can't go past Travelocity. Take your pick of 400 air carriers and 1,000,000 properties around the world to create the ultimate adventure — it's really that easy.
Why should I purchase my Winchester vacation bundle via Travelocity?
We take the hassle out of travel planning. Whether you're seeking a new destination to wander around or want to make sure you get the best price on offer, we're here to assist. Our 24/7 customer support, quality service and Price Match Guarantee mean you can confidently book with Travelocity.
Can I save on my Winchester car rental if I combine it with my hotel or flight?
Booking a Winchester vacation package with Travelocity is one of the simplest ways to save your time and money. Choose a flight, car and hotel, or any combination of them, and enjoy great discounts. You could also add on experiences and tours. Once you've picked up the keys to your rental car, venture out of the neighborhood and see what this place has to offer. About 95 mi from Winchester, Times Square is worth a road trip.

Photos of local treasures

Browse Winchester vacation photos for more inspiration