Deals on vacations and trips to Winchester

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Winchester flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Landing Apartments New Haven

Landing Apartments New Haven

3 out of 5
West New Haven
Save 100% on your flight
Price was $1,160, price is now $766 per person
$766
per person
May 22 - May 29
found 17 hours ago
Roundtrip flight included
Atlanta (ATL) 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.
Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
North End
Save 100% on your flight
Price was $4,179, price is now $2,500 per person
$2,500
per person
May 22 - May 29
found 17 hours ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
This vacation home doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, a garden, and a communal living room are also on offer.
Hyatus Luxury Residences City Crossing

Hyatus Luxury Residences City Crossing

4 out of 5
The Hill
Save 100% on your flight
Price was $2,171, price is now $1,571 per person
$1,571
per person
May 22 - May 29
found 17 hours ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
This aparthotel features a 24-hour gym and a seasonal outdoor pool. Traveling for business? Take advantage of the free WiFi in public areas, laundry service, and conference center. Enjoy the a rooftop terrace and perks like free self parking and a free area shuttle.
Luxury Furnished Apartments by Hyatus Downtown at Yale

Luxury Furnished Apartments by Hyatus Downtown at Yale

3.5 out of 5
The Hill
Save 100% on your flight
Price was $1,978, price is now $1,446 per person
$1,446
per person
May 22 - May 29
found 17 hours ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
This aparthotel features a gym and a rooftop terrace. Guests will appreciate free perks like free self parking and WiFi in public areas. A garden, express check-out, and dry cleaning are also on offer.

Top Winchester hotels deals

Waterfront Cottage at Highland Lake w/dock

Waterfront Cottage at Highland Lake w/dock

Winsted CT
Get rates
This cottage includes a garden and barbecue grills.
Kitchen
Free WiFi
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
$147 nightly
The price is $169 total per night
$169 total
Apr 11 - Apr 12
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
Apr 12 - Apr 13
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
Delamar West Hartford

Delamar West Hartford

4 out of 5
1 Memorial Road West Hartford CT
Free Cancellation
Reserve now, pay when you stay
$392 nightly
The price is $448 total per night
$448 total
Apr 26 - Apr 27
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
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
$153 nightly
The price is $176 total per night
$176 total
Apr 12 - Apr 13
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
Extended Stay America Suites Hartford Farmington

Extended Stay America Suites Hartford Farmington

2.5 out of 5
1 Batterson Park Rd Farmington CT
$94 nightly
The price is $108 total per night
$108 total
Apr 12 - Apr 13
Total with taxes and fees
This hotel features free WiFi in public areas, laundry facilities, and free self parking. Enjoy the free on-the-go breakfast each morning. A safe deposit box is provided and the front desk is staffed around-the-clock.
Breakfast included
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

American Mural Project

You can spend time studying the exhibits at American Mural Project in Winchester.

American Mural Project

Frequently asked questions

How much are vacation packages to Winchester?
You'll be pleasantly surprised — you can unwind in Winchester for a mere $766. 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

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