Lakeville Vacation Packages 2026 from $435

Lakeville flight + hotel vacation packages

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

The Cromwell Inn

$435

per person

Dec 17 - Dec 20

found 17 hours ago

Roundtrip flight included

Chicago (MDW) to Hartford (BDL)

This hotel doesn't skimp on freebies - guests receive free English breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of the 24-hour business center and free internet in public areas. Enjoy the gym and conveniences like a 24-hour front desk and laundry facilities.

Delamar West Hartford

$1,390

per person

Dec 22 - Dec 26

found 6 hours ago

Roundtrip non-stop flight included

Dallas (DFW) to Hartford (BDL)

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.

Simsbury 1820 House

Simsbury Center

$934

per person

Dec 22 - Dec 26

found 6 hours ago

Roundtrip non-stop flight included

Dallas (DFW) to Hartford (BDL)

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.

Holiday Inn Express Vernon - Manchester by IHG

$800

per person

Dec 22 - Dec 26

found 6 hours ago

Roundtrip non-stop flight included

Dallas (DFW) to Hartford (BDL)

This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.

Candlewood Suites Windsor Locks Bradley Arpt by IHG

$682

per person

Dec 22 - Dec 26

found 6 hours ago

Roundtrip non-stop flight included

Dallas (DFW) to Hartford (BDL)

This hotel doesn't skimp on freebies - guests receive free WiFi, free self parking, and a free airport shuttle. Families will appreciate the bowling alley and barbecue grills. Business travelers can take advantage of the 24-hour business center.

Top Lakeville hotels deals

Interlaken Inn & Resort

74 Interlaken Road Lakeville CT

$254 nightly

$292 total

Dec 1 - Dec 2

Total with taxes and fees

This hotel features a full-service spa, 3 outdoor tennis courts, and a restaurant. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the gym and perks like free self parking.

Pool

Spa

Summer Lake Cottage, private beach, Berkshire Hills, small village

Lakeville CT

Get rates

This cottage features a garden, laundry facilities, and barbecue grills.

Kitchen

Washer

Quality Inn Great Barrington

372 Main Street Great Barrington MA

Free Cancellation

$70 nightly

$79 total

Dec 2 - Dec 3

Total with taxes and fees

A gym, free self parking, and free newspapers are featured at this hotel. Guests will appreciate free perks like on-the-go breakfast and WiFi in public areas. A picnic area and barbecue grills are also provided.

Breakfast included

Parking included

Prospect Berkshires

50 Prospect Lake Rd Egremont MA

$255 nightly

$285 total

Nov 30 - Dec 1

Total with taxes and fees

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Enjoy the sauna and perks like free self parking and free WiFi. A coffee shop, a grocery/convenience store, and a picnic area are also on offer.

Pool

Spa

the Alander

7519 NY-22 Copake NY

$165 nightly

$185 total

Nov 20 - Nov 21

Total with taxes and fees

A restaurant and a bar/lounge are featured at this lodge. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls. Take advantage of the free self parking.

Pet friendly

Parking included

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

249 Stockbridge Rd Great Barrington MA

Free Cancellation

Reserve now, pay when you stay

$161 nightly

$179 total

Nov 8 - Nov 9

Total with taxes and fees

This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like continental breakfast and free self parking.

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.

Stay near popular Lakeville attractions

Lime Rock Park

9.2/10 (30 reviews)

Catch an event at Lime Rock Park during your trip to Lakeville. Discover the waterfalls and countryside in this relaxing area.

See properties

Frequently asked questions

How much are vacation packages to Lakeville?

Travelocity has great package deals to Lakeville, as well as flights and hotels, starting at just $435. With all that extra cash, you could include some awesome tours or perhaps even tack on a couple of extra days to your exciting adventure.

How long should my Lakeville vacation be?

Typically, people stay 2 nights in Lakeville. But that mightn't be long enough for you. If you'd like to explore some of the area's hidden gems, how about adding another few nights to your travel schedule?

Where can I get the best vacation package deals for Lakeville?

You can't beat Travelocity when it comes to crafting your Lakeville package deal. There are at least 400 air carriers and 1,000,000 properties worldwide to choose from. Lock in your trip now and get ready to tick another destination off your to-do list.

Why should I book my Lakeville vacation package with Travelocity?

We've got 24/7 support, top-notch service and a Price Match Guarantee. Life is all about the journey — and we have enticing destinations for you to journey to all across the globe. Wander with us and make your hip pocket happy.

Can I save on my Lakeville car rental if I combine it with a hotel or flight?

Bundling your hotel, car and flight into a Lakeville vacation package is the best way to score an incredible deal. Plus, having your own car rental gives you total freedom to make your way to all the landmarks you want to see. Sitting 90 mi away from Lakeville, Times Square is one attraction that should be on your must-do list. Put together a driving playlist and make a day trip of it.

Which airport is best for Lakeville?

Many people choose to fly into Bradley Intl. Airport (BDL), 40 mi east of downtown Lakeville. Others prefer Albany Intl. Airport (ALB) (55 mi away from central Lakeville) or Tweed - New Haven Regional Airport (HVN) (55 mi away from central Lakeville).

Where should I stay when visiting Lakeville?

The Interlaken Inn & Resort is the number one choice of many visitors. Book as soon as possible to avoid missing out.