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

Ashland Holiday Rentals

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Our top choices for Ashland holiday rentals

1. Cold Spring Plymouth Resort

Cold Spring Plymouth Resort
3.5 star property
Ashland
9.2 out of 10, Wonderful, (274 reviews)
"Had a great weekend stay."
United States
Armand
The price is NZ$211
includes taxes & fees
1 Nov - 2 Nov
Cold Spring Plymouth Resort

2. Cute Lower Level Cedar Lodge Room with Balcony & Lake Views!

Cute Lower Level Cedar Lodge Room with Balcony & Lake Views!
Weirs Beach
9.2 out of 10, Wonderful, (7 reviews)
"Property was very clean, had very comfortable beds and a wonderful view. "
United States
Crystal
The price is NZ$382
includes taxes & fees
28 Oct - 29 Oct
Cute Lower Level Cedar Lodge Room with Balcony & Lake Views!

3. Mountain Cabin with long range views, privacy, and more.

Mountain Cabin with long range views, privacy, and more.
Campton
9.4 out of 10, Exceptional, (12 reviews)
"Great location, beautiful views, and everything we could want, from amenities to the communication."
United States
Robert G.
The price is NZ$494
includes taxes & fees
2 Nov - 3 Nov
Mountain Cabin with long range views, privacy, and more.

4. Best value on Newfound Lake NH 2 day min

Best value on Newfound Lake NH 2 day min
Bristol
9.0 out of 10, Wonderful, (34 reviews)
"Perfect stay! Exactly as described, great little cabin and was perfect for a family weekend "
United States
Kasey C.
The price is NZ$732
includes taxes & fees
15 Oct - 16 Oct
Best value on Newfound Lake NH 2 day min

5. Cedar Lodge Room 2 Queen Beds & Private Balcony

Cedar Lodge Room 2 Queen Beds & Private Balcony
Weirs Beach
The price is NZ$448
includes taxes & fees
3 Nov - 4 Nov
Cedar Lodge Room 2 Queen Beds & Private Balcony

6. Weirs beach retreat

Weirs beach retreat
Weirs Beach
9.8 out of 10, Exceptional, (8 reviews)
"Just a minutes drive to the waterfront and shops. Great location "
United States
Wayne W.
The price is NZ$492
includes taxes & fees
18 Oct - 19 Oct
Weirs beach retreat

7. The Gnome Home Cottage located near white mountain NH

The Gnome Home Cottage located near white mountain NH
Campton
9.6 out of 10, Exceptional, (66 reviews)
"Stay was great ! Little small for multiple people but great place for a couple getaway weekend"
United States
Jesse C.
The price is NZ$546
includes taxes & fees
21 Oct - 22 Oct
The Gnome Home Cottage located near white mountain NH

8. Family Friendly, King Bed, Beach Access, Fire Pit, Game Room

Family Friendly, King Bed, Beach Access, Fire Pit, Game Room
Bristol
10.0 out of 10, Exceptional, (6 reviews)
"Nicely maintained, clean property that was very comfortable for 6 of us attending a wedding right down the street at the inn. "
United States
Becky M.
The price is NZ$762
includes taxes & fees
13 Oct - 14 Oct
Family Friendly, King Bed, Beach Access, Fire Pit, Game Room

9. Gilford Perfect Getaway Pool, WIFI & Free Parking

Gilford Perfect Getaway Pool, WIFI & Free Parking
Laconia
8.4 out of 10, Very good, (7 reviews)
"Very nice place, easily located near everything. Would definitely stay here again."
United States
Katherine B.
The price is NZ$393
includes taxes & fees
15 Oct - 16 Oct
Gilford Perfect Getaway Pool, WIFI & Free Parking

10. Lake Winnipesaukee Home for Fall & Winter Fun

Lake Winnipesaukee Home for Fall & Winter Fun
3.0 star property
Moultonborough
The price is NZ$814
includes taxes & fees
13 Oct - 14 Oct
Lake Winnipesaukee Home for Fall & Winter Fun

11. Meredith Bay - Brand New 2nd and 3rd floor Apartment in Private Home

Meredith Bay - Brand New 2nd and 3rd floor Apartment in Private Home
Meredith
10.0 out of 10, Exceptional, (176 reviews)
"We loved our stay. Very clean and in a great location in Meredith."
United States
Rebecca R.
The price is NZ$639
includes taxes & fees
14 Oct - 15 Oct
Meredith Bay - Brand New 2nd and 3rd floor Apartment in Private Home

12. White Mountain Cozy Cottage with Touch of Modern

White Mountain Cozy Cottage with Touch of Modern
Campton
9.4 out of 10, Exceptional, (55 reviews)
"The cottage was perfect for our long weekend getaway. It was more spacious than expected and convenient location. The host is very responsive and accommodating. Would stay again!"
United States
Emily F.
The price is NZ$562
includes taxes & fees
12 Oct - 13 Oct
White Mountain Cozy Cottage with Touch of Modern

13. Getaway on Tenney Mountain! Beautiful 2-bedroom+ Condo for the entire family!

Getaway on Tenney Mountain! Beautiful 2-bedroom+ Condo for the entire family!
Plymouth
The price is NZ$774
includes taxes & fees
21 Oct - 22 Oct
Getaway on Tenney Mountain! Beautiful 2-bedroom+ Condo for the entire family!

14. Squam waterfront 2 bed 2 bath (Suite 8)

Squam waterfront 2 bed 2 bath (Suite 8)
Holderness
10.0 out of 10, Exceptional, (3 reviews)
"Right on the water! Great views, wonderful beach/dock, great little place to stay!"
United States
colette c.
The price is NZ$791
includes taxes & fees
12 Oct - 13 Oct
Squam waterfront 2 bed 2 bath (Suite 8)

15. Waterfront 2 bedroom 2 bath at Squam (Suite 11)

Waterfront 2 bedroom 2 bath at Squam (Suite 11)
Holderness
8.4 out of 10, Very good, (6 reviews)
"Thanks so much for hosting us! we have been coming to squam for 20+ years and never stayed at the boulders. The space was great for the price and right on the lake. We had no issues whatsoever and would highly recommend for anyone looking for a cabin type weekend by the water. "
United States
Anonymous traveller
The price is NZ$772
includes taxes & fees
14 Oct - 15 Oct
Waterfront 2 bedroom 2 bath at Squam (Suite 11)

16. Escape to Central Escape’s 2-bedroom option, perfectly located in New Hampshire’s Lakes Region. Enjoy a private year-round hot tub, spacious backyard with yard games, and easy access to downtown Meredith, Squam Lake, and summer concerts.

Escape to Central Escape’s 2-bedroom option, perfectly located in New Hampshire’s Lakes Region. Enjoy a private year-round hot tub, spacious backyard with yard games, and easy access to downtown Meredith, Squam Lake, and summer concerts.
Holderness
10.0 out of 10, Exceptional, (2 reviews)
"Everything was wonderful!! "
United States
Scott O.
The price is NZ$784
includes taxes & fees
27 Oct - 28 Oct
Escape to Central Escape’s 2-bedroom option, perfectly located in New Hampshire’s Lakes Region. Enjoy a private year-round hot tub, spacious backyard with yard games, and easy access to downtown Meredith, Squam Lake, and summer concerts.

17. Meredith Bay - Brand New 1st Floor Apartment In Private Home

Meredith Bay - Brand New 1st Floor Apartment In Private Home
Meredith
10.0 out of 10, Exceptional, (53 reviews)
"The apartment was very comfortable and just as pictured. We had a wonderful stay! It’s a great location for walking in Meredith and an easy drive to ski at Gunstock. "
United States
Karen O.
The price is NZ$694
includes taxes & fees
13 Oct - 14 Oct
Meredith Bay - Brand New 1st Floor Apartment In Private Home

18. Cedar Lodge Room-Private Balcony Close to Weirs!

Cedar Lodge Room-Private Balcony Close to Weirs!
Weirs Beach
9.6 out of 10, Exceptional, (5 reviews)
"Very clean, quiet and good location to points of interest. Nice beds!!"
United States
Deborah J.
The price is NZ$432
includes taxes & fees
11 Oct - 12 Oct
Cedar Lodge Room-Private Balcony Close to Weirs!

19. Cedar Lodge condo with mountain & lake Winnipesauke views!

Cedar Lodge condo with mountain & lake Winnipesauke views!
Weirs Beach
9.2 out of 10, Wonderful, (58 reviews)
"The room was adequate. Clean but not superclean!"
United States
Walter
The price is NZ$495
includes taxes & fees
14 Oct - 15 Oct
Cedar Lodge condo with mountain & lake Winnipesauke views!

20. Cozy Studio w/ Pool. Close to Weirs Beach, Concerts,Lake, & Gunstock Mountain

Cozy Studio w/ Pool. Close to Weirs Beach, Concerts,Lake, & Gunstock Mountain
Laconia
10.0 out of 10, Exceptional, (32 reviews)
The price is NZ$606
includes taxes & fees
19 Oct - 20 Oct
Cozy Studio w/ Pool. Close to Weirs Beach, Concerts,Lake, & Gunstock Mountain
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 Ashland Hotel Reviews

Find out more about Ashland

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Ashland holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Ashland. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Ashland. Seeing all the best attractions is bound to make you fall in love with Ashland. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Ashland short-term rentals, that won’t be hard to do.

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.