Lakeville Holiday Rentals

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Holiday Rentals in Lakeville

Charming apartment 7 minute walk to downtown
10.0 out of 10, Exceptional, (15)
"Everything about our stay was great - Corin and Jen were wonderful hosts. The place is spotless, cozy, comfy. Love that they were right next to the Green Way Trail along the river. Will absolutely stay there again! "
United States
Kate B.
The price is AU$411
includes taxes & fees
29 Oct - 30 Oct
Charming apartment 7 minute walk to downtown
Cozy 3 Flr Private 1 Bdrm Apt Tree Line View
9.6 out of 10, Exceptional, (4)
"The check-in process was easy and all instructions were clear. Jonathan, the owner, was very responsive and easy to get a hold of if I had any questions. The place was cute, clean, and perfect for what I needed (a place to stay during my medical school rotation). As the review says, it is not ideal for taller guests as the roof slopes down in certain areas, but I found the place cozy."
United States
Nicole N.
The price is AU$425
includes taxes & fees
26 Oct - 27 Oct
Cozy 3 Flr Private 1 Bdrm Apt Tree Line View
Las Flores Villa
5.0 star property
10.0 out of 10, Exceptional, (1)
The price is AU$2,419
includes taxes & fees
27 Oct - 28 Oct
Las Flores Villa
The Blue Elm - A Historic Berkshire Cottage
10.0 out of 10, Exceptional, (11)
"Everything was great...and beautiful!"
United States
Nicole L.
The price is AU$644
includes taxes & fees
28 Oct - 29 Oct
The Blue Elm - A Historic Berkshire Cottage
CT Gate House Goshen CT, Gate House Goshen CT
2.5 star property
9.8 out of 10, Exceptional, (7)
"The property was great and the house was huge even for all 12 of us "
United States
Ryan L.
The price is AU$1,026
includes taxes & fees
4 Nov - 5 Nov
CT Gate House Goshen CT, Gate House Goshen CT
Home in Great Barrington
9.8 out of 10, Exceptional, (24)
"Crisp and clean with a great location.Wonderful choice."
United States
Richard B.
The price is AU$475
includes taxes & fees
23 Nov - 24 Nov
Home in Great Barrington
Mid Century Modern Studio w/ Full Kitchen - Newly Built
9.6 out of 10, Exceptional, (5)
"Super cute, clean, and convenient for our quick trip to The Millbrook School."
United States
Carol H.
The price is AU$448
includes taxes & fees
27 Oct - 28 Oct
Mid Century Modern Studio w/ Full Kitchen - Newly Built
Hoppy Hill Farm House
9.4 out of 10, Exceptional, (3)
"The cabin was perfect. Had everything we needed and clear directions. "
United States
Jocelyn L.
The price is AU$331
includes taxes & fees
2 Nov - 3 Nov
Hoppy Hill Farm House
The Brooks Motel: Exceptional Suite
9.2 out of 10, Wonderful, (5)
"Clean, industrial, very comfy bed, easy to book and to check in and out. Would stay again."
United States
Deidre H.
The price is AU$314
includes taxes & fees
24 Oct - 25 Oct
The Brooks Motel: Exceptional Suite
The Jefferson Guest House, Spacious, Special Views
10.0 out of 10, Exceptional, (8)
"I stayed here for four nights, including one with my son, and it was fantastic.Everything is brand new, clean, and beautifully appointed, with every amenity you could want."
United States
Jennifer A.
The price is AU$587
includes taxes & fees
26 Oct - 27 Oct
The Jefferson Guest House, Spacious, Special Views
Cheerful 3-bedroom cottage with woodstove
10.0 out of 10, Exceptional, (39)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is AU$703
includes taxes & fees
11 Nov - 12 Nov
Cheerful 3-bedroom cottage with woodstove
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. "
United States
Tom S.
The price is AU$1,114
includes taxes & fees
3 Nov - 4 Nov
Guesthouse Cabin vacation rentals in Berkshire County
Great Barrington Get Away
9.4 out of 10, Exceptional, (24)
"The host was very communicative and responsive during our arrival and check out. The listing and everything was as it said we were very pleased with both the location of the home and the actual home itself and the property walking distance to town truly cannot say enough. Thank you for Your hospitality. Our family is very grateful. "
United States
Amy B.
The price is AU$748
includes taxes & fees
27 Oct - 28 Oct
Great Barrington Get Away
Cozy. Clean. Free bagel shop.
10.0 out of 10, Exceptional, (10)
"The perfect location for a stay in Great Barrington. The house is so well done and very comfortable!"
United States
Carly F.
The price is AU$946
includes taxes & fees
4 Nov - 5 Nov
Cozy. Clean. Free bagel shop.
The George is an elegant restored home in the Hudson Valley
9.2 out of 10, Wonderful, (5)
"Clean, comfortable, private, and plenty of room. Hosts went above and beyond to make our stay easy and memorable."
United States
Polly J.
The price is AU$1,459
includes taxes & fees
30 Oct - 31 Oct
The George is an elegant restored home in the Hudson Valley
Charming 3-bedroom apartment on 2nd floor in Millbrook NY, right in the village
10.0 out of 10, Exceptional, (1)
"Tanya goes above and beyond for her guests. Thanks so much for the stay!"
United States
Lindsay S.
The price is AU$764
includes taxes & fees
24 Oct - 25 Oct
Charming 3-bedroom apartment on 2nd floor in Millbrook NY, right in the village
Cozy Riverfront Escape in Great Barrington - "Whiskers on the Water"
9.0 out of 10, Wonderful, (2)
"Close to a great bakery and near to a farm market and shopping mall. "
United States
Cristine C.
The price is AU$403
includes taxes & fees
3 Nov - 4 Nov
Cozy Riverfront Escape in Great Barrington - "Whiskers on the Water"
Whispering Estate Guest House - A Romantic Countryside Getaway
10.0 out of 10, Exceptional, (4)
"Beautiful property and great location. A true retreat. "
United States
Andrea B.
The price is AU$1,880
includes taxes & fees
4 Nov - 5 Nov
Whispering Estate Guest House - A Romantic Countryside Getaway
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
10.0 out of 10, Exceptional, (1)
"Everything was well taken care of, the hosts were extremely nice, and the area is perfect! The city is also different and really cute! Will come back for sure!"
United States
Roberta
The price is AU$2,194
includes taxes & fees
3 Nov - 4 Nov
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
rural, serene + sophisticated space
10.0 out of 10, Exceptional, (7)
"Beautiful property with unique accommodations in the Hudson Valley"
United States
BRIAN PATRICK M.
The price is AU$696
includes taxes & fees
10 Nov - 11 Nov
rural, serene + sophisticated space
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.
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Top Lakeville Hotel Reviews

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, 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 favourite 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 depend 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 AU$403 per night. Entering your travel dates in the search wizard might find you 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?

Cozy Riverfront Escape in Great Barrington - "Whiskers on the Water": This holiday home rental outside of Lakeville is located on a river, and has a fireplace, a garden and laundry facilities to put you at ease in your new surroundings. It has 3 bedrooms, in addition to a kitchen with a stovetop and a microwave.

How many holiday rentals will I find in Lakeville?

Expedia has 14 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.