Exclusive Highland Lake Vacation Deals

Highland Lake vacation package deals

Price found within the past 48 hours. Click for updated prices.
The Surfside Hotel

The Surfside Hotel

2 out of 5
Lordship
Price was $380, price is now $341 per person
$341
per person
Feb 12 - Feb 14
found 1 day ago
Roundtrip flight included
Houston (IAH) to New Haven (HVN)
A restaurant, free self parking, and wedding services are among this hotel's amenities. WiFi in public areas is free. Luggage storage is also provided.
Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
North End
Save 100% on your flight
Price was $2,378, price is now $1,465 per person
$1,465
per person
Jan 29 - Feb 2
found 20 hours ago
Roundtrip flight included
Denver (DEN) 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.

Landing Modern 2bd, Gym

3 out of 5
West New Haven
Price was $964, price is now $814 per person
$814
per person
Feb 13 - Feb 17
found 1 day ago
Roundtrip flight included
Chicago (ORD) 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.
Omni New Haven Hotel at Yale

Omni New Haven Hotel at Yale

4 out of 5
Downtown New Haven
Price was $821, price is now $696 per person
$696
per person
Feb 13 - Feb 17
found 1 day ago
Roundtrip flight included
Chicago (ORD) 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.
Graduate by Hilton New Haven

Graduate by Hilton New Haven

4 out of 5
Downtown New Haven
Price was $823, price is now $705 per person
$705
per person
Feb 13 - Feb 17
found 1 day ago
Roundtrip flight included
Chicago (ORD) to New Haven (HVN)
A restaurant and a bar/lounge are featured at this hotel. WiFi in public areas is free. A coffee shop and luggage storage are also provided.
Cambria Hotel New Haven University Area

Cambria Hotel New Haven University Area

3 out of 5
West River
Price was $646, price is now $575 per person
$575
per person
Mar 5 - Mar 8
found 15 hours ago
Roundtrip non-stop flight included
Houston (HOU) to New Haven (HVN)
This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Self parking, a lobby fireplace, and a computer station are also offered.

Frequently asked questions

How much are vacation packages to Highland Lake?
Let Travelocity take the worry out of arranging your visit to Highland Lake. Check out our fantastic $341 package deal and save both time and money. With your flights and hotel sorted, you can concentrate on the fun parts of your adventure — like discovering those well-known attractions!
Where can I get the best vacation package deals for Highland Lake?
There are sensational Highland Lake package deals to be gained with Travelocity. Did you know we partner with as many as 400 airlines and 1,000,000 properties worldwide? Keep that in mind the next time you're ready to tick another place off your list.
Why should I purchase my Highland Lake vacation bundle via Travelocity?
Because life is one amazing journey, and we have everything you could hope for to help get you on your way. With our superb service and Price Match Guarantee, you can book with confidence. What's more, you can rest easy on the road knowing you can reach us with our 24/7 customer support.

Top Highland Lake hotel deals

The Litchfield Inn

The Litchfield Inn

4 out of 5
432 Bantam Road Litchfield CT
Free Cancellation
Reserve now, pay when you stay
$274 nightly
The price is $315 total per night
$315 total
Jan 20 - Jan 21, 2026
Total with taxes and fees
A full-service spa and a 24-hour gym are featured at this smoke-free hotel. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like cooked-to-order breakfast and free self parking.
Breakfast included
Spa
Simsbury 1820 House

Simsbury 1820 House

4 out of 5
731 Hopmeadow St Simsbury CT
Free Cancellation
Reserve now, pay when you stay
$174 nightly
The price is $200 total per night
$200 total
Dec 30 - Dec 31
Total with taxes and fees
The bed & breakfast's indoor pool, gym, and 2 bars/lounges are among the featured amenities. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy a meal from the restaurant and perks like free continental breakfast and free self parking.
Pool
Breakfast included
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
$118 nightly
The price is $136 total per night
$136 total
Dec 30 - Dec 31
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
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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.