Book Holiday Homes in Dalton

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Featured Holiday Homes in Dalton

Spectacular views and close to Great Barrington.

Spectacular views and close to Great Barrington.

Great Barrington
Located in Great Barrington, this vacation home is within a 5-minute drive of Housatonic River and Housatonic River Walk.
Spectacular views and close to Great Barrington.
Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!

Lanesborough
The price is AU$361 per night from 30 Dec to 31 Dec
AU$361
includes taxes & fees
30 Dec - 31 Dec
Located in Lanesborough, this vacation home is in the mountains, within a 15-minute drive of Crane Museum of Papermaking and Berkshire Athenaeum.
Berkshire Village Carriage House - Super Private!!
Berkshire Ski House on Lake Garfield w/HT By Great Barrington

Berkshire Ski House on Lake Garfield w/HT By Great Barrington

Monterey
Located in Monterey, this vacation home is within a 5-minute drive of Beartown State Forest and Bidwell House Museum.
Berkshire Ski House on Lake Garfield w/HT By Great Barrington
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Beautiful Berkshire Farm House on 160+ Acres

Beautiful Berkshire Farm House on 160+ Acres

Great Barrington
Located in Great Barrington, this vacation home is on the waterfront, within a 15-minute drive of W.E.B. Du Bois Boyhood Homesite and Mahaiwe Performing Arts ...
Beautiful Berkshire Farm House on 160+ Acres
Peace and quiet on the lake

Peace and quiet on the lake

Becket
With a stay at this vacation home in Becket (Sherwood Forest), you'll be within a 10-minute drive of Pyramid Lake and Jacob's Pillow.
Peace and quiet on the lake
Quintessential 6-BR Berkshires Lodge

Quintessential 6-BR Berkshires Lodge

Becket
When you stay at this vacation home in Becket, you'll be within a 10-minute drive of Pyramid Lake and Jacob's Pillow.
Quintessential 6-BR Berkshires Lodge
Amore Estate -  beautiful room with many places to explore and relax in.

Amore Estate - beautiful room with many places to explore and relax in.

Lenox
With a stay at this vacation home in Lenox, you'll be within a 5-minute drive of Wyndhurst Golf & Club and Berkshire Scenic Railway Museum.
Amore Estate - beautiful room with many places to explore and relax in.
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!

Beautiful Lenox Home, 3 Mi to Shakespeare & Co!

Lenox
Located in Lenox, this vacation home is within a 15-minute walk of Pleasant Valley Wilderness Sanctuary and Kennedy Park.
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!
A Grand property in Historic Stockbridge

A Grand property in Historic Stockbridge

Stockbridge
A stay at this vacation home places you in the heart of Stockbridge, steps from Housatonic River and Mission House.
A Grand property in Historic Stockbridge
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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.

Dalton Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Dalton vacation homes are the perfect way for you to wing it.

Holiday houses in Dalton let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Dalton in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Dalton adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Dalton with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Dalton vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Dalton Holiday Homes essential information

Accommodation
276 Holiday Homes
Lowest Price
AU$158
Highest Price
AU$361
Popular accommodation
Spectacular views and close to Great Barrington., Berkshire Village Carriage House - Super Private!!, Berkshire Ski House on Lake Garfield w/HT By Great Barrington , Beautiful Berkshire Farm House on 160+ Acres, Peace and quiet on the lake, Quintessential 6-BR Berkshires Lodge, Amore Estate - beautiful room with many places to explore and relax in., Beautiful Lenox Home, 3 Mi to Shakespeare & Co!, A Grand property in Historic Stockbridge

Top trending hotels in Dalton

Hotel Downstreet

Hotel Downstreet

3 out of 5
40 Main St, North Adams, MA
Fully refundableReserve now, pay when you stay
The price is AU$207 per night from 5 Jan to 6 Jan
AU$207
includes taxes & fees
5 Jan - 6 Jan 2025
A stay at Hotel Downstreet places you in the heart of North Adams, steps from Western Gateway Heritage State Park and 3 minutes by foot from Massachusetts Museum ...
Hotel Downstreet
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 out of 5
461 Pittsfield Rd, Lenox, MA
Fully refundableReserve now, pay when you stay
The price is AU$173 per night from 30 Dec to 31 Dec
AU$173
includes taxes & fees
30 Dec - 31 Dec
Located in Lenox, The Yankee, Trademark Collection by Wyndham is on the Strip, a 4-minute drive from Bousquet Ski Area and 7 minutes from Shakespeare and ...
The Yankee, Trademark Collection by Wyndham
Life House Berkshires

Life House Berkshires

3.5 out of 5
194 Pittsfield Rd, Lenox, MA
Fully refundableReserve now, pay when you stay
The price is AU$158 per night from 1 Jan to 2 Jan
AU$158
includes taxes & fees
1 Jan - 2 Jan 2025
Located in Lenox, Life House Berkshires is within a 15-minute walk of Kennedy Park and Pleasant Valley Wilderness Sanctuary.
Life House Berkshires
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The Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street, Stockbridge, MA
Fully refundableReserve now, pay when you stay
The price is AU$360 per night from 5 Jan to 6 Jan
AU$360
includes taxes & fees
5 Jan - 6 Jan 2025
When you a stay at The Red Lion Inn in Stockbridge, you'll be in the historical district, within a 5-minute walk of Housatonic River and Mission House.
The Red Lion Inn
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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.

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^Subject to availability and chosen travel dates.