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Glenwood Holiday Rentals

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Check prices for these dates

Tonight
24 Dec - 25 Dec
Tomorrow
25 Dec - 26 Dec
This weekend
26 Dec - 28 Dec
Next weekend
2 Jan - 4 Jan

Our top choices for Glenwood holiday rentals

Smart TV
Cabin with private beach access to Lake Minnewaska

Cabin with private beach access to Lake Minnewaska

Cabin with private beach access to Lake Minnewaska
Glenwood
10.0 out of 10, Exceptional, (16)
"A very nice and relaxing place to stay! very clean and well kept. "
United States
Ryan C.
The price is HK$595
HK$1,265 total
includes taxes & fees
4 Jan - 5 Jan 2026
Cabin with private beach access to Lake Minnewaska
Sports court
Steps to Lake Minnewaska, downtown & city Splash Pad!! Lake Minnewaska/Glenwood

Steps to Lake Minnewaska, downtown & city Splash Pad!! Lake Minnewaska/Glenwood

Steps to Lake Minnewaska, downtown & city Splash Pad!! Lake Minnewaska/Glenwood
Glenwood
10.0 out of 10, Exceptional, (22)
"Enjoyed our stay!"
United States
Bryon B.
The price is HK$735
HK$1,858 total
includes taxes & fees
5 Jan - 6 Jan 2026
Steps to Lake Minnewaska, downtown & city Splash Pad!! Lake Minnewaska/Glenwood
Exterior
O'Halloran House-Feathered Acres Learning Farm & Inn

O'Halloran House-Feathered Acres Learning Farm & Inn

O'Halloran House-Feathered Acres Learning Farm & Inn
Belgrade
10.0 out of 10, Exceptional, (1)
"We stayed at Feathered Acres relatively last minute (thanks Trisha!!) after making some travel plan changes and we had such a wonderful time. Travelled with mom and my two toddlers and we all had a blast. We stayed in the smaller studio unit the first night and the larger two bedroom unit the second night and both were so cute, thoughtful and comfortable! The studio can easily house 3 adults if needed and had a curtained off area where we stuck our toddler's pack n plays, and is a bit more...
United States
Karie C.
The price is HK$1,555
HK$2,249 total
includes taxes & fees
5 Jan - 6 Jan 2026
O'Halloran House-Feathered Acres Learning Farm & Inn
Terrace/patio
Lake Latoka Home w/Paddle boards, Kayaks, Paddle Boat, Pool Table, Dock, Sunsets

Lake Latoka Home w/Paddle boards, Kayaks, Paddle Boat, Pool Table, Dock, Sunsets

Lake Latoka Home w/Paddle boards, Kayaks, Paddle Boat, Pool Table, Dock, Sunsets
2.0 star property
Alexandria
10.0 out of 10, Exceptional, (17)
"Our family loved their stay. Great layout with a beautiful clean home and impressive lake setting. The paddle boat, kayaks, paddle boards and pool table were an extra bonus! "
United States
Diane S.
The price is HK$2,975
HK$7,165 total
includes taxes & fees
27 Dec - 28 Dec
Lake Latoka Home w/Paddle boards, Kayaks, Paddle Boat, Pool Table, Dock, Sunsets
Property grounds
Ruby's Red Door Retreat on Swenson Lake welcomes you to serenity

Ruby's Red Door Retreat on Swenson Lake welcomes you to serenity

Ruby's Red Door Retreat on Swenson Lake welcomes you to serenity
2.0 star property
Pennock
9.8 out of 10, Exceptional, (15)
"Although it was a rainy stay, my husband and kids had a great time fishing while the baby and I stayed warm and cozy inside by the fire. It was a perfect little birthday getaway, such a cute cottage everyone loved it!"
United States
Candice E.
The price is HK$1,555
HK$2,831 total
includes taxes & fees
7 Jan - 8 Jan 2026
Ruby's Red Door Retreat on Swenson Lake welcomes you to serenity
Interior
Large Historic Estate on the shores of Lake Winona

Large Historic Estate on the shores of Lake Winona

Large Historic Estate on the shores of Lake Winona
Alexandria
10.0 out of 10, Exceptional, (25)
"A wonderful and charming house for a writers’ retreat! The hosts are very responsive, and the rooms are lovely."
United States
Cristina P.
The price is HK$4,305
HK$8,346 total
includes taxes & fees
27 Dec - 28 Dec
Large Historic Estate on the shores of Lake Winona
Fridge, microwave, oven, stovetop
Spacious 5-bedroom Osakis lakefront house/guest house with dock, WiFi, AC, spa

Spacious 5-bedroom Osakis lakefront house/guest house with dock, WiFi, AC, spa

Spacious 5-bedroom Osakis lakefront house/guest house with dock, WiFi, AC, spa
Osakis
9.0 out of 10, Wonderful, (2)
"Great time with our family group of 4 adults & 4 kidsA beautifully maintained home was well equipped with all the amenities needed for our stay. The guest house has an L-shaped screened porch with furniture & lots of outdoor toys & games to play & the fire pit was awesomeJohn, the owner, was easy to work with & prompt to answer any questions or concerns"
United States
Rose H.
The price is HK$2,255
HK$5,395 total
includes taxes & fees
2 Jan - 3 Jan 2026
Spacious 5-bedroom Osakis lakefront house/guest house with dock, WiFi, AC, spa
Fridge, microwave, oven, stovetop
Fall Colors Up North! Fishing • Winery • Games

Fall Colors Up North! Fishing • Winery • Games

Fall Colors Up North! Fishing • Winery • Games
Kensington
10.0 out of 10, Exceptional, (12)
"Cabin was very clean and had everything we needed! "
United States
Sara H.
The price is HK$1,478
HK$3,424 total
includes taxes & fees
5 Jan - 6 Jan 2026
Fall Colors Up North! Fishing • Winery • Games
Smart TV, fireplace, ping pong, computer monitors
Experience Luxury, leisure, and lakefront living for the whole family.

Experience Luxury, leisure, and lakefront living for the whole family.

Experience Luxury, leisure, and lakefront living for the whole family.
Alexandria
9.6 out of 10, Exceptional, (33)
"Such a fantastic stay. Raj and Geethika took excellent care of us when we had questions and were very accommodating overall. 9:30 AM was a little early for checkout but that didn’t dampen the great time we had here. Highly recommend!"
United States
Mark S.
The price is HK$4,301
HK$5,895 total
includes taxes & fees
29 Dec - 30 Dec
Experience Luxury, leisure, and lakefront living for the whole family.
Interior
Brand New Grand Home on Lake Miltona Alexandria 12 Person Hot Tub

Brand New Grand Home on Lake Miltona Alexandria 12 Person Hot Tub

Brand New Grand Home on Lake Miltona Alexandria 12 Person Hot Tub
Alexandria
10.0 out of 10, Exceptional, (10)
"This is the nicest VRBO I have ever stayed in. "
United States
Mark J.
The price is HK$5,314
HK$10,098 total
includes taxes & fees
2 Jan - 3 Jan 2026
Brand New Grand Home on Lake Miltona Alexandria 12 Person Hot Tub
Exterior
Lake Victoria, Hilltop Lodge , Panoramic views overlooking the lake.

Lake Victoria, Hilltop Lodge , Panoramic views overlooking the lake.

Lake Victoria, Hilltop Lodge , Panoramic views overlooking the lake.
Alexandria
9.0 out of 10, Wonderful, (31)
"Nice place to stay! Would go back. "
United States
Tory L.
The price is HK$2,722
HK$3,764 total
includes taxes & fees
11 Jan - 12 Jan 2026
Lake Victoria, Hilltop Lodge , Panoramic views overlooking the lake.
2 bedrooms, iron/ironing board, WiFi, bed sheets
Charming 4kingsize bed house in Benson with AC,WIFI,CableTV,Firepit,Washer/Dryer

Charming 4kingsize bed house in Benson with AC,WIFI,CableTV,Firepit,Washer/Dryer

Charming 4kingsize bed house in Benson with AC,WIFI,CableTV,Firepit,Washer/Dryer
benson
The price is HK$778
HK$2,136 total
includes taxes & fees
6 Jan - 7 Jan 2026
Charming 4kingsize bed house in Benson with AC,WIFI,CableTV,Firepit,Washer/Dryer
Exterior
Scaler Energy Field Therapy cozy bedroom in the outskirts of Alexandria Mn.

Scaler Energy Field Therapy cozy bedroom in the outskirts of Alexandria Mn.

Scaler Energy Field Therapy cozy bedroom in the outskirts of Alexandria Mn.
Alexandria
The price is HK$2,139
HK$2,631 total
includes taxes & fees
7 Jan - 8 Jan 2026
Scaler Energy Field Therapy cozy bedroom in the outskirts of Alexandria Mn.
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 Glenwood Hotel Reviews

Best Western Alexandria Inn

Best Western Alexandria Inn

10/10 Excellent
"Yes"
Kathy 1-night trip
Posted 3 days ago
Best Western Alexandria Inn

Find out more about Glenwood

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

  • View our selection of featured holiday rentals in Glenwood
  • Use the map to find apartments and other holiday homes in the Glenwood neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Glenwood while they last

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

Frequently asked questions

Can I find a holiday rental in Glenwood?

Yes, there are holiday rentals close to the most popular sights in Glenwood, or you can select a more secluded option if you're looking for a relaxing stay. Glenwood is known for its lake views and restaurants. Make sure you have time to check out the shopping and forests during your trip.

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

Home in the Center of the City!: This holiday home rental outside of Glenwood is located in the city centre, and has a patio, a garden and air conditioning to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family.

How many holiday rentals are there in Glenwood?

With 9 Expedia holiday rentals, you're guaranteed to find just the right place for your Glenwood stay.

What’s there to see and do in Glenwood?

Lake Minnewaska and Barsness Park are a couple of scenic spots to enjoy the outdoors, whereas Pope County Historical Museum is one of the cultural attractions. While here, Peter Sunset Beach Resort and Minnewaska Golf Club are other places worth a visit.

What are holiday rentals like in Glenwood?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Glenwood. Holiday rentals feature amenities such as hot tubs, fire pits and patios so you'll feel just like you're at home. If you're concerned about cleanliness, a holiday rental can provide a sense of privacy away from public hotel lifts and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive option for small groups.