Plan your trip

A town nestled in a valley with a river running through it, surrounded by lush green hills.

Search Holiday Rentals in Ashland

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Save instantly and earn perks with One Key

    Learn about One Key

  • Be picky

    Search almost a million properties worldwide

  • Check prices for these dates

    Check prices for these dates, 14 – 15 December 2026

    View in a map

    Our top choices for Ashland holiday rentals

    1. Cold Spring Plymouth Resort

    A row of brown single-story buildings with a parking lot in front.

    2. Lake Winnipesaukee Condo w/ Beach Access!

    A spacious living room with a fireplace, large windows with a view of boats, and a cozy seating area.

    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.

    View all properties

    Find holiday rentals that suit your style

    Cabins

    Apartments

    Aparthotels

    Cottages

    Condos

    Chalets

    Villas

    Top Ashland Hotel Reviews

    Fairfield by Marriott Inn & Suites Plymouth White Mountains

    A stone fire pit surrounded by Adirondack chairs and a seating area with skis and snowboards leaning against a wall.

    Cold Spring Plymouth Resort

    A row of brown single-story buildings with a parking lot in front.

    Inn On Golden Pond

    A patio with a stone fire pit, outdoor furniture, and a play structure in the background.

    The Ballard House Inn

    A covered porch with two rocking chairs facing a sunset view.

    Best Western Plymouth Inn-White Mountains

    An indoor swimming pool with lounge chairs and a gazebo.

    The Nutmeg Inn

    A cozy living room with two patterned sofas, a coffee table with a book, a fireplace, and a Christmas wreath.

    Squam Lake Inn

    A two-story house with a porch, surrounded by a garden with small lights.

    Meredith Inn

    A living room with a fireplace, a blue armchair, a red sofa, and a coffee table.

    The Common Man Inn Plymouth

    A cozy log cabin interior with a large bed, a fireplace, and a view of a lake.

    Holiday Inn Express Hotel & Suites Tilton - Lakes Region by IHG

    A Holiday Inn Express building with a covered entrance and multiple floors.

    The Sunny G B&B

    A two-story house with green shutters, a front porch, and a driveway.

    The Tea Rose Inn at Plymouth

    A large, two-story house with a prominent front porch, a chimney, and a flag.

    Colonel Spencer Inn

    A yellow house with a white picket fence, outdoor seating with chairs and a table, and a gravel patio.

    Hampton Inn & Suites Tilton

    A modern hotel lobby with a seating area, a flat-screen TV, and a reception desk.

    TownePlace Suites by Marriott Gilford

    A hotel with a modern design, featuring a prominent entrance and large windows.

    The Lake Estate on Winnisquam

    A poolside area with lounge chairs, a wicker basket, and a view of a lake with trees and mountains in the background.

    Find out more about Ashland

    Everything you need to know about Ashland 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 Ashland 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 Ashland holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

    Ashland holiday rentals: An excellent choice for every season

    Whenever you want to travel, a warm welcome awaits you in Ashland. 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 Ashland 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 Ashland holiday rentals we have selected for you start as low as £96 per night. Entering your travel dates in the search wizard you might find even better deals!

    How to find incredible deals on Ashland rentals

    At Expedia, we put the best Ashland 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 Ashland 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 Ashland 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 Ashland. 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 Ashland?

    Yes, there are holiday rentals in Ashland close to Ashland Railroad Station Museum, or you can select a more secluded option if you're looking for a relaxing stay. Nature enthusiasts will enjoy the mountain landscape in Ashland. Make sure you have time to check out the architecture and lake views during your trip.

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

    Stunning Waterfront Home with Boat Dock, swim, boating. Bike & skiing nearby.: This holiday home rental outside of Ashland is located on a lake, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of games in this rental home to help you unwind.

    How many holiday rentals are there in Ashland?

    Choose from 9 Expedia holiday rentals in Ashland for a memorable holiday.

    What’s there to see and do in Ashland?

    Cultural attractions include Whipple House Museum and Pauline E Glidden Toy Museum, whereas Little Squam Lake and Whitten Woods Trailhead are a couple of picturesque spots to enjoy the outdoors. Other places in town to visit include Ashland Railroad Station Museum and Riveredge Marina.

    What’s a holiday rental in Ashland like?

    Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Ashland. Holiday rentals provide amenities such as laundry facilities and kitchens so you'll feel just like you're at home. If you're concerned about cleanliness, a holiday rental can provide a sense of security away from public hotel lifts and busy reception areas while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a popular option for a small group gathering.