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

Ashland Vacation Rentals

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Ashland vacation rentals

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

1. Cold Spring Plymouth Resort

Cold Spring Plymouth Resort
3.5 star property
Ashland
9.2 out of 10, Wonderful, (272 reviews)
"Had a great weekend stay."
United States
Armand
The price is ￥20,892
￥22,668 total
includes taxes & fees
Oct 25 - Oct 26
Cold Spring Plymouth Resort
A narrow hallway leading to a bathroom with a sink and mirror. A bed is visible in the adjacent room.

2. Cute Cedar Lodge Studio with Balcony & Lake Views!

Cute Cedar Lodge Studio with Balcony & Lake Views!
Weirs Beach
9.2 out of 10, Wonderful, (21 reviews)
"The room was nice. Great view of the lake."
United States
Brandy a.
The price is ￥15,454
￥36,123 total
includes taxes & fees
Oct 28 - Oct 29
Cute Cedar Lodge Studio with Balcony & Lake Views!
A beach with clear water, a sandy shore, and a line of trees in the background.

3. Lake Getaway: Walk Across Street to Private Beach!

Lake Getaway: Walk Across Street to Private Beach!
Gilford
9.4 out of 10, Exceptional, (28 reviews)
"the property was a great location for my stay Host was good at returning calls/text replying to questions and concerns will rent again.. thanks"
United States
Laura C.
Lake Getaway: Walk Across Street to Private Beach!
A beach with people relaxing and sunbathing, a lifeguard tower, and a sandy shore lined with trees.

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, (33 reviews)
"Perfect stay! Exactly as described, great little cabin and was perfect for a family weekend "
United States
Kasey C.
The price is ￥24,861
￥65,166 total
includes taxes & fees
Oct 6 - Oct 7
Best value on Newfound Lake NH 2 day min
A swimming pool with lounge chairs and umbrellas, surrounded by a fence and greenery.

5. 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 ￥16,574
￥44,872 total
includes taxes & fees
Oct 12 - Oct 13
Weirs beach retreat
A riverbank with a wooden bridge, surrounded by dense trees.

6. 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 ￥24,861
￥48,897 total
includes taxes & fees
Oct 14 - Oct 15
The Gnome Home Cottage located near white mountain NH
A wooden deck with a table and two wicker chairs, a window with a view of trees and mountains, and a sign that reads "It's A Wonderful Life".

7. 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 ￥26,708
￥66,486 total
includes taxes & fees
Oct 6 - Oct 7
Family Friendly, King Bed, Beach Access, Fire Pit, Game Room
A lakeside cabin with a dock, surrounded by dense trees and a sandy beach area with lounge chairs.

8. 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 ￥50,181
￥72,138 total
includes taxes & fees
Oct 12 - Oct 13
Squam waterfront 2 bed 2 bath (Suite 8)
A beach with clear water, a dock, and boats.

9. 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 traveler
The price is ￥50,181
￥70,389 total
includes taxes & fees
Oct 13 - Oct 14
Waterfront 2 bedroom 2 bath at Squam (Suite 11)
A swimming pool with blue chairs and umbrellas, surrounded by a white wall with blue windows.

10. 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 ￥14,205
￥34,767 total
includes taxes & fees
Oct 15 - Oct 16
Gilford Perfect Getaway Pool, WIFI & Free Parking
A riverbank with a wooden bridge, surrounded by dense trees.

11. 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 ￥24,719
￥49,086 total
includes taxes & fees
Oct 13 - Oct 14
White Mountain Cozy Cottage with Touch of Modern
A cozy living room with a brown leather sofa, a wooden coffee table, and a fish-themed wall decoration.

12. Lake Winnipesaukee Home for Fall & Winter Fun

Lake Winnipesaukee Home for Fall & Winter Fun
3.0 star property
Moultonborough
The price is ￥18,311
￥72,247 total
includes taxes & fees
Oct 13 - Oct 14
Lake Winnipesaukee Home for Fall & Winter Fun
A beach with picnic tables and lounge chairs, a stone wall, and a view of the lake and distant mountains.

13. Lake view, Private Beach, Private concert entrance, pool, Gunstock ski resort

Lake view, Private Beach, Private concert entrance, pool, Gunstock ski resort
Gilford
9.8 out of 10, Exceptional, (35 reviews)
"Great location, specially for concerts or enjoying the beach. Some road noise."
United States
Estuardo
The price is ￥21,941
￥43,331 total
includes taxes & fees
Nov 2 - Nov 3
Lake view, Private Beach, Private concert entrance, pool, Gunstock ski resort
Living area

14. 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 ￥28,413
￥68,679 total
includes taxes & fees
Oct 20 - Oct 21
Getaway on Tenney Mountain! Beautiful 2-bedroom+ Condo for the entire family!
A kitchen with wooden cabinets, a marble countertop, a sink, a stove, and a hanging light fixture.

15. Plymouth! Close to campus, downtown and Speare

Plymouth! Close to campus, downtown and Speare
Plymouth
The price is ￥41,041
￥89,402 total
includes taxes & fees
Oct 6 - Oct 7
Plymouth! Close to campus, downtown and Speare
A two-story house with a covered porch and a small deck.

16. 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 ￥38,358
￥66,282 total
includes taxes & fees
Oct 13 - Oct 14
Meredith Bay - Brand New 1st Floor Apartment In Private Home
A large building with multiple sections, surrounded by snow-covered ground and trees, overlooking a large body of water.

17. 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 ￥24,656
￥47,866 total
includes taxes & fees
Oct 13 - Oct 14
Cedar Lodge condo with mountain & lake Winnipesauke views!
A beach with three wooden lounge chairs facing a lake, surrounded by trees.

18. Squam Lake 3 bed 3 bath (Suite #7)

Squam Lake 3 bed 3 bath (Suite #7)
Holderness
10.0 out of 10, Exceptional, (3 reviews)
"Great spot for a fun long weekend."
United States
katherine c.
The price is ￥65,808
￥94,991 total
includes taxes & fees
Oct 12 - Oct 13
Squam Lake 3 bed 3 bath (Suite #7)
A large building with multiple sections, surrounded by snow-covered ground and trees, with a lake and mountains in the background.

19. Cedar Lodge Room 2 Queen Beds & Private Balcony

Cedar Lodge Room 2 Queen Beds & Private Balcony
Weirs Beach
The price is ￥17,364
￥39,060 total
includes taxes & fees
Oct 6 - Oct 7
Cedar Lodge Room 2 Queen Beds & Private Balcony
A wooden cabin with a hot tub and a deck area.

20. 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 ￥37,032
￥69,467 total
includes taxes & fees
Oct 26 - Oct 27
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.
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

The Naswa Resort

The Naswa Resort

10/10 Excellent
"Cute cottage! Easy access to both parking and beach/bar, great view! Full kitchen with all the amenities."
cheryl 1-night trip
Posted 5 hours ago
The Naswa Resort

Find out more about Ashland

Search for holiday rentals in Ashland on Expedia! You can easily find your home rentals, villas, holiday apartments in Ashland using one of the methods below:

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Look no further and take a look at our great range of rental properties in Ashland!

Frequently asked questions

Can I find vacation rentals in Ashland?

Yes, we offer vacation rentals in Ashland near Ashland Railroad Station Museum, or you can choose 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 vacation rentals that Ashland has to offer?

Stunning Waterfront Home with Boat Dock, swim, boating. Bike & skiing nearby.: Visitors like this Ashland vacation home rental. It is located on a lake and has a balcony, a garden, and a barbecue grill 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 you can cook with friends or family. Make the most of the selection of games in this rental home to help you unwind.

How many vacation rentals are there in Ashland?

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

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 vacation rental in Ashland like?

A vacation rental is a private property you can stay in for a couple of days or more in Ashland. Vacation rentals offer extras such as hot tubs, fire pits, and patios so you'll have everything you want. If you're concerned about a sanitized environment, vacation rentals can offer a sense of security away from shared hotel elevators and busy front desks while still allowing you the experience of travel. You'll also get more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive option for family gatherings.