Preston Vacation Rentals from $665: Search Short-Term Rentals

Q: What's the top vacation rental in Preston?

Private 2 Acre Waterfront Family Retreat with Pool & Pier : This vacation home rental near Preston is located on the waterfront and has an outdoor pool, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 8 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of books.

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Our top choices for Preston vacation rentals

1. Sailwinds Loft at Cambridge Creek

Cambridge

Sharon D.

$240 nightly

Sep 21 - Sep 22

Total with taxes and fees

2. Turnbridge Manor

Denton

Glenn S.

$575 nightly

Sep 21 - Sep 22

Total with taxes and fees

3. Waterfront • Heated Decks • Workspace • EV Charging • Home Gym • Downtown

Cambridge

mike

$518 nightly

Sep 21 - Sep 22

Total with taxes and fees

4. The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge

Downtown Cambridge

Kristen S.

$363 nightly

Sep 23 - Sep 24

Total with taxes and fees

5. Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Cambridge

Robert

$372 nightly

Sep 28 - Sep 29

Total with taxes and fees

6. WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE

Cambridge

Anonymous traveler

$619 nightly

Sep 21 - Sep 22

Total with taxes and fees

7. WATERFRONT!! HOT TUB 3 bedroom Oasis on 2+ acres - Sleeps 8

Cambridge

Jill C.

$579 nightly

Sep 22 - Sep 23

Total with taxes and fees

8. Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

Grasonville

Robin

$460 nightly

Sep 21 - Sep 22

Total with taxes and fees

Coffee/tea maker, fridge, microwave, oven

9. Waterfront Getaway with Dock

Woolford

Meagan G.

$228 nightly

Oct 4 - Oct 5

Total with taxes and fees

10. Sunset Breezes - quiet waterfront retreat

Dorchester County

John C.

$437 nightly

Sep 27 - Sep 28

Total with taxes and fees

11. The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

Woolford

Ramon A.

$627 nightly

Oct 6 - Oct 7

Total with taxes and fees

12. Family Retreat at Lansdowne Manor

Centreville

Emily C.

$419 nightly

Sep 30 - Oct 1

Total with taxes and fees

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Top Preston Hotel Reviews

Days Inn & Suites by Wyndham Seaford

10/10 Excellent

"Nice"

Wylder Tilghman Island

8/10 Good

"Property is well maintained and clean. The rooms are small but adequate. Our only fault was the restaurant pricing. Dishes are at least 25 to 40 percent upvharged. For example, a bowl of gazpacho was priced at $18 . If crab eas added it would have been $15 more for a grand total of $33 for a bowl of soup. Outrageous. I’ve been to 5 star restaurants and never paid that much for a bowl of soup. The chicken entree was $30 and the chicken consisted of 2 small chicken finger type pieces. No full breast or thigh/leg. Drinks definitely upcheged. Drive a bit down the road and eat at Chesapeake seafood or drive into town. If you don’t feel comfortable driving at night, go in and have a late lunch or get takeout."

Find out more about Preston

Everything you need to know about Preston vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Preston vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 Preston vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Preston vacation rentals: An excellent choice for every season

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

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $665 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Preston rentals

At Expedia, we put the best Preston vacation 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 Preston 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 Preston vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Preston. 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 vacation rentals in Preston?

Yes, there are vacation rentals near top attractions in Preston, or you can choose a more remote option if you'd like a relaxing place to stay.

What's the top vacation rental in Preston?

Private 2 Acre Waterfront Family Retreat with Pool & Pier: This vacation home rental near Preston is located on the waterfront and has an outdoor pool, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 8 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of books.

What’s there to see and do in Preston?

Gilpin's Point Landing and Williston Lake are a couple of lovely local spots to get outside and enjoy nature. In the larger area, you’ll find Academy of the Arts and Avalon Theatre.

What’s a vacation rental in Preston like?

Vacation rentals are private properties where you can stay for a couple of days or more in Preston. Vacation rentals feature extras such as kitchens and laundry facilities so you'll have all the comforts of home. If you're concerned about cleanliness, vacation rentals can provide a sense of seclusion away from public hotel elevators and lobbies bustling with people while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is an attractive choice for small groups.

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