Dorset Beach Vacations 2026

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Top Beach vacation packages in Dorset

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

Saratoga Casino Hotel

$545

per person

Oct 16 - Oct 19

found 11 hours ago

Roundtrip flight included

Chicago (CHI) to Albany (ALB)

9.4/10 Exceptional! (1,019 reviews)

South Shire

$575

per person

Oct 16 - Oct 19

found 11 hours ago

Roundtrip flight included

Chicago (CHI) to Albany (ALB)

9.2/10 Wonderful! (128 reviews)

It is a classic house that is full of antique s and fine wood working.

Reviewed on Aug 17, 2026

Lodges At Cresthaven

$668

per person

Oct 16 - Oct 19

found 11 hours ago

Roundtrip flight included

Chicago (CHI) to Albany (ALB)

9.4/10 Exceptional! (623 reviews)

Overall is really nice to stay here with my family.

Reviewed on Aug 17, 2026

Urban Cowboy Lodge

$927

per person

Oct 23 - Oct 25

found 1 day ago

Roundtrip flight included

Chicago (CHI) to Albany (ALB)

9.4/10 Exceptional! (251 reviews)

Room has unique personality, however the room is too small for what I paid for. And we've been told the room will be cleaned daily, never happened. The overall experience is tranquil weekend getaway.

Reviewed on Aug 15, 2026

The Equinox Golf Resort & Spa

Manchester Village Historic District

Save 100% on your flight

$1,879

per person

Oct 16 - Oct 19

found 11 hours ago

Roundtrip flight included

Chicago (CHI) to Albany (ALB)

7.4/10 Good! (656 reviews)

We loved this hotel, really nice amenities, great rooms. I wish we had planned less activities and spent more time at the hotel. If you want to stay in the hotel, plan to spend a day in the hotel. Breakfast ends at 11 and bar closes at around 10 depending on crowd.

Reviewed on Aug 16, 2026

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See all available trips from Columbus to Dorset

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5* Beach vacations in Dorset

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

Urban Cowboy Lodge

$927

per person

Oct 23 - Oct 25

found 1 day ago

Roundtrip flight included

Chicago (CHI) to Albany (ALB)

9.4/10 Exceptional! (251 reviews)

Room has unique personality, however the room is too small for what I paid for. And we've been told the room will be cleaned daily, never happened. The overall experience is tranquil weekend getaway.

Reviewed on Aug 15, 2026

Don't see what you're looking for?

See all available trips from Columbus to Dorset

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3 Night Beach vacations in Dorset

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

Saratoga Casino Hotel

$545

per person

Oct 16 - Oct 19

found 11 hours ago

Roundtrip flight included

Chicago (CHI) to Albany (ALB)

9.4/10 Exceptional! (1,019 reviews)

South Shire

$575

per person

Oct 16 - Oct 19

found 11 hours ago

Roundtrip flight included

Chicago (CHI) to Albany (ALB)

9.2/10 Wonderful! (128 reviews)

It is a classic house that is full of antique s and fine wood working.

Reviewed on Aug 17, 2026

Lodges At Cresthaven

$668

per person

Oct 16 - Oct 19

found 11 hours ago

Roundtrip flight included

Chicago (CHI) to Albany (ALB)

9.4/10 Exceptional! (623 reviews)

Overall is really nice to stay here with my family.

Reviewed on Aug 17, 2026

Don't see what you're looking for?

See all available trips from Columbus to Dorset

View all trips

4 Night Beach vacations in Dorset

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

The Ponds at Foxhollow

Save 100% on your flight

$706

per person

Oct 22 - Oct 26

found 1 day ago

Roundtrip flight included

Chicago (CHI) to Albany (ALB)

8.6/10 Excellent! (145 reviews)

Quiet property. Convenient location.

Reviewed on Aug 2, 2026

The Cornell Inn, Lenox & The Berkshires

Save 100% on your flight

$903

per person

Oct 22 - Oct 26

found 21 hours ago

Roundtrip flight included

Chicago (CHI) to Albany (ALB)

9.2/10 Wonderful! (1,002 reviews)

Prospect Berkshires

Save 100% on your flight

$1,393

per person

Oct 22 - Oct 26

found 1 day ago

Roundtrip flight included

Chicago (CHI) to Albany (ALB)

9.8/10 Exceptional! (40 reviews)

It was beautiful but quite expensive. There was no housekeeping included so trash was not picked up and the breakfasts were grossly overpriced!

Reviewed on Aug 19, 2026

Don't see what you're looking for?

See all available trips from Columbus to Dorset

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How do I book the best Dorset beach vacation packages?

Life’s a beach when you dive into our brilliant Dorset beach vacation deals. Chuck a check in the filter boxes to find ocean views, pools, and resorts just a short saunter from the sizzling sands.

How can I find cheap beach vacations in Dorset?

A rental steps from the shore creates an amazingly affordable Dorset beach vacation. Seaside sojourns during low season start from $545. Prices and availability are subject to change. Additional terms may apply.

When should I book a Dorset beach holiday?

For a bustling beach break, book in . For a less crowded coast, is the time to turn up.

How can I book the best family beach vacations in Dorset?

With a flick of a finger, the family-friendly filter brings you the best breaks on offer for the whole brood. Look out for kids’ clubs, waterparks, and other incredible extras for a vacay the little ones will love.

How do I find a Dorset beachfront vacation?

Check the beachfront filter and, bam, the best available oceanside resorts will appear before your eyes. Along with the incredible view, when you book a beachfront resort, you can get from the lapping waves to your patio lounger in a matter of moments.

Can I book a package including a Dorset vacation beach house rental?

Hit up the vacation rental filter to book your dream beach house. Once you’ve selected the most alluring abode, add your flights and car rental for the perfect package deal.

Can I find Dorset beach vacation deals?

Sort your search results by deals to delight in amazing Dorset beach vacation offers. If you want more pizzazz for your pennies, travel outside the high season or stay a little further from the shoreline.

Can I book a Dorset beach trip with free cancellation and/or flexible dates?

Just like the Dorset tides, plans change. Filter by payment option to find trips with free cancellation. Buy now, pay later options are also available for full-on flexibility.

Why should I book my Dorset beach vacation with Expedia?

Relax long before you see the shore with simple search, fantastic filters, and more great deals than there are grains of sand in Dorset. (OK, maybe not that last part.)

Top Beach Dorset Hotels

8-bedroom vacation home just 16 minutes from Golf Club at Equinox

Dorset VT

26 min walk from Green Mountain National Forest

At this vacation home, get ready to stroll along the shoreline in Dorset, as you'll be close to the beach.

9.6/10 Exceptional! (18 reviews)

"The stay was nice! We had plenty of space for our big family. The kitchen gathering area was very spacious."

Reviewed on Oct 25, 2025

Charming pet-friendly, Meadow View Cottage in heart of historic Dorset VT!

Dorset VT

14 min drive from Green Mountain National Forest

Stay at this cottage in Dorset. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Green Mountain National Forest and Dorset Playhouse are ...

10/10 Exceptional! (42 reviews)

"Wish all rentals were this great!The house is charming, neat, soulful, nicely decorated and the kitchen is incredibly well stocked with everything a chef could want. This feels like a person's home, not an impersonal rental. The owner was super responsive when we had a few questions. Would stay here ..."

Reviewed on Apr 17, 2026

See all 2,020 properties in Dorset

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.