Holiday Rentals in Lakeville

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

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In one month
In two months
In three months

Holiday Rentals in Lakeville

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

9.4 out of 10, Exceptional, (82)
"The house has rustic charm and sits right on the lake. It is a beautiful peaceful spot. "
Summer Lake Cottage, private beach, Berkshire Hills, small village

Waterfront Cabin w Firepit, Dock, Deck, BBQ. Direct Lake Access! Pet-friendly!

8.8 out of 10, Excellent, (24)
"The cabin was great! Exactly as described and pictured. The kitchen was well stocked with all the basic cooking instruments and utensils. We had a blast and would absolutely come back."
Waterfront Cabin w Firepit, Dock, Deck, BBQ. Direct Lake Access! Pet-friendly!

Lakefront Fall Foliage in New England Just 2 Hours From NYC

10.0 out of 10, Exceptional, (82)
"Great location and fully equipped cabin! I hope to return sometime soon Everything was perfect!"
Lakefront Fall Foliage in New England Just 2 Hours From NYC

The Blue Elm - A Historic Berkshire Cottage

10.0 out of 10, Exceptional, (10)
"Everything was great...and beautiful!"
The price is €352
includes taxes & fees
5 Oct - 6 Oct
The Blue Elm - A Historic Berkshire Cottage

Whispering Estate Guest House - A Romantic Countryside Getaway

10.0 out of 10, Exceptional, (3)
"Beautiful property and great location. A true retreat. "
The price is €1,058
includes taxes & fees
5 Oct - 6 Oct
Whispering Estate Guest House - A Romantic Countryside Getaway

Premiere Berkshire Country Estate w/ Private Pool & Tennis Court - 5 mins to GB!

10.0 out of 10, Exceptional, (55)
"We loved Manor Lane! It had every amenity you could ask for. The house is fun and charming and there are thoughtful touches everywhere you look! We had fun watching movies in the living room, playing games in the lounge, cooking family meals in the spectacular kitchen and playing tennis in the sunshine. A perfect 10!"
Premiere Berkshire Country Estate w/ Private Pool & Tennis Court - 5 mins to GB!

Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!

10.0 out of 10, Exceptional, (27)
"Spacious, welcoming, so well stocked, we felt lucky to find the property."
Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!

Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT

9.8 out of 10, Exceptional, (21)
"We had a wonderful time, the property is lovely and the house is delightful."
Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT

The Goshen Glass Chalet

9.6 out of 10, Exceptional, (40)
"The chalet was great. Plenty of room, very cozy and in a very quiet neighborhood community. "
The Goshen Glass Chalet

Reset and Relax in Luxury Cottage

10.0 out of 10, Exceptional, (43)
"We love everything about this place! This is the second time we’ve stayed here and will definitely stay again next time we are in the area."
Reset and Relax in Luxury Cottage

Guesthouse Cabin vacation rentals in Berkshire County

10.0 out of 10, Exceptional, (9)
"Really enjoyed the cabin. The pictures don’t do the view justice as it’s an amazing vista overlooking the Berkshires. "
The price is €607
includes taxes & fees
5 Oct - 6 Oct
Guesthouse Cabin vacation rentals in Berkshire County

Bluebird Valley Farmhouse

10.0 out of 10, Exceptional, (69)
"We stayed at the property while attending a family wedding. The house and yard were perfect. The best Vrbo we’ve ever stayed at. Would stay there again!"
Bluebird Valley Farmhouse

Amazing 2-bedroom apartment sunny and quiet in Great Barrington

9.4 out of 10, Exceptional, (32)
"Perfect place for what we needed. Loved the location."
Amazing 2-bedroom apartment sunny and quiet in Great Barrington

Antique Farmhouse Totally Restored

10.0 out of 10, Exceptional, (91)
"Enjoyed the property, location and charming house that was well stocked with everything we needed."
Antique Farmhouse Totally Restored

Stunning 1860 Farmhouse, Private Pond & Hot Tub!

8.4 out of 10, Very good, (7)
"The house is located in a tranquil and exquisite setting with sound of crickets and cicadas and full views of the stars at night. It’s a drive to any coffee or restaurants but worth it if you are looking for a peaceful place to stay. "
Stunning 1860 Farmhouse, Private Pond & Hot Tub!

Charming cottage with lake access, wood burning fire place, and WiFi

2.0 star property
9.0 out of 10, Wonderful, (8)
"Oriana was awesome and I look forward to staying there again."
Charming cottage with lake access, wood burning fire place, and WiFi

The Race Mountain House

2.0 star property
9.2 out of 10, Wonderful, (5)
"I spent my 60th birthday with a few friends at Mountain House and it was even better than I dreamed. The comfort and simplicity of the decor along with the mountain views. A must for those who like simple elegance."
The Race Mountain House

Peaceful, Post and Beam Loft, Sleeps 9

10.0 out of 10, Exceptional, (20)
"Amazing Place to stay. Beautiful location and house is amazing. Only one issue is the loft gets a bit hot the AC couldn't quite keep up. Will recommend and hopefully stay again next year. "
Peaceful, Post and Beam Loft, Sleeps 9

Stay Lakeside This Summer!

9.8 out of 10, Exceptional, (76)
"Beautiful lake views, comfy and cozy house! We had a wonderful time. Thank you for sharing your home with us. "
Stay Lakeside This Summer!

Family House On Highland Lake with Dock

10.0 out of 10, Exceptional, (28)
"Awesome location, plenty of space in the house, clean, and the host was very responsive. Will definitely stay here again when in Connecticut. "
Family House On Highland Lake with Dock
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Lakeville Hotel Reviews

Find out more about Lakeville

Find out more about Lakeville

Everything you need to know about Lakeville holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Lakeville holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Lakeville holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Lakeville holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Lakeville. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Lakeville holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Lakeville holiday rentals we have selected for you start as low as €352 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Lakeville rentals

At Expedia, we put the best Lakeville holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Lakeville rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Lakeville holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Lakeville. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find holiday rentals in Lakeville?

Yes, there are holiday rentals close to the most popular sights in Lakeville, or you can select a more secluded option if you're looking for a relaxing stay. Lakeville is known for its restaurants and museums.

What are some of the best holiday rentals that Lakeville has to offer?

Whispering Estate Guest House - A Romantic Countryside Getaway: This holiday home rental outside of Lakeville offers a fireplace, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most of books in this rental home to help you unwind.

How many holiday rentals will I find in Lakeville?

Expedia has 15 holiday rentals for your stay in Lakeville.

What’s there to see and do in Lakeville?

While exploring the area, visit family-friendly sights like Harney and Sons Tea Tasting Room, or get outside and enjoy nature at Mount Frissell. Holley-Williams House Museum and Lime Rock Park are other places to visit while you're in town.

What’s a holiday rental in Lakeville like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Lakeville. Holiday rentals offer extras like WiFi and washers and dryers so you'll have all the conveniences of home. If you're concerned about a sanitised environment, a holiday rental can provide a sense of safety away from shared hotel lifts and busy reception areas while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a hotel, which makes a holiday rental a popular choice for a small group gathering.