Round Top Cottage: Find The Top Holiday Cottages in Round Top

A mountainous landscape with dense forests and a rocky cliff.

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Our top choices for Round Top cottages

1. Warm cozy country cottage nestled beneath the mountains, woodstove, Catskill

Catskill

Athena P.

includes taxes & fees

1 Sept - 2 Sept

2. Cozy 2-bedroom cottage in enchanting Catskill Mountains

Catskill

includes taxes & fees

11 Aug - 12 Aug

3. Charming Cottage in the Heart of Catskill & Pet Friendly

Catskill

Dave P.

includes taxes & fees

26 Aug - 27 Aug

4. Charming loft cottage in tranquil Germantown with WiFi, AC

Germantown

Lisa B.

includes taxes & fees

9 Sept - 10 Sept

5. Close to skiing in Windham and Hunter, hiking, lakes, 20+restaurants

Maplecrest

Yichen

includes taxes & fees

11 Aug - 12 Aug

6. Streamside Cottage Half Mile to Town of Woodstock

Woodstock

Anonymous traveller

includes taxes & fees

11 Aug - 12 Aug

7. Sleepy Hollow Lake Home w/ Deck, Pool Access!

Coxsackie

audrey

includes taxes & fees

19 Aug - 20 Aug

8. Boho Hot Tub Cottage | Pet-Friendly | Hudson Valley

Stottville

includes taxes & fees

14 Aug - 15 Aug

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Top Round Top Hotel Reviews

Pocketbook Hotel and Bath

10/10 Excellent

"Beautiful property, would stay again"

Hotel Vienna

10/10 Excellent

"Great weekend visit at Hotel Vienna with our 2 small dogs! Check in and check out were super easy, staff was helpful and accommodating, and the property was really quiet, very clean and super well maintained. The bathrooms were obviously recently renovated and very tastefully done, the bed was firm and linens soft and comfy. Breakfast was pastries, cereal, and yogurt; all were high quality, fresh and delicious. Cappuccino and tea were lovely. Shower pressure could have been a bit better, but that was literally the only downside. We did not have a chance to use the pool, but it looked very clean, located in a nice, stand-alone building with windows and skylights. Barrel sauna is just outside on the deck, and both are is surrounded by beautiful landscaping. The main building also has two sunny, well furnished decks, and there are fire pits with Adirondack chairs located about the property, and there's direct access to the Windham Path and dog park. Sad I missed the free Saturday morning yoga, but I'll definitely try to make it next time. All in all, this hotel was perfect, peaceful, and we'll definitely be back to explore all the things we missed!"

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

10/10 Excellent

"We had the most beautiful amazing stay! It was a bit hard to find our cabin when we got there because there was no maps or anything that we could access while driving with no reception in the area, but we eventually found it. Our air-conditioning didn’t work well in the unit and it was quite hot but other than that it was perfect and we will absolutely stay again, hopefully in the fall!"

Wylder Hotel Windham

10/10 Excellent

"The staff were wonderful and went out of their way to make sure you had whatever you wanted. There are plenty of things to do right at the hotel and you are right by the mountains if you want to take advantage of that. The pool is heated and you can have drinks by the pool. There are several locations for fire pits and the staff will help you get a raging fire going immediately upon request. The golf course was simply beautiful and if that is your thing, absolutely a must. The restaurant on the grounds was terrific as was the bakery for breakfast and goodies. The buildings themselves are 150 years old and are lovely to check out just for that. I would certainly return in the future."

St. Charles Hotel

8/10 Good

"It’s basic, it’s simple, it gets the job done. I didn’t use the shower, but the sink water pressure was a little lower than preferred. It’s in a fantastic location at a great price for what you need. Clean rooms. Didn’t think it would be clean when I walked in, but it totally was. 2 small kids wanted to watch TV, and the WiFi wasn’t strong enough, that was the main issue for my stay. It did however work for iPads. What I will commend was that the owner (presumably) picked up the phone right away and sent the manager to help. It didn’t for the TV, but at least the iPads worked. A few WiFi extenders is likely all that’s needed. I’d definitely stay again. Thanks again St, Charles! And owner and manager."

voco James Newbury Hudson Valley by IHG

10/10 Excellent

"Excellent experience! Such a beautiful location. Room was absolutely perfect and staff was so helpful and accommodating. Breakfast was so good!! Such a perfect setting. I had to work a little in the morning and the lobby area was so perfect. Will be back, this time for fun not work!"

Find out more about Round Top

Round Top Cottages information

Number of reviews	397
Accommodation	186 Cottages
Lowest Price	AU$362
Highest Price	AU$1,118

Frequently asked questions

How much do cottages in Round Top cost?

Cottages in Round Top range between AU$362 and AU$1,118 per night. These stays offer a chance to get reacquainted with nature — at a price you can afford. This price was available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.

What is there to do in Round Top near my cottage?

Round Top has enough experiences and sights to keep you on the hop for weeks, starting with Hunter Mountain. Kaaterskill Falls, Bailiwick Ranch and Discovery Zoo and Indian Head Mountain are other fantastic attractions. If you have more time, Blackhead Mountain Country Club and Platte Clove Preserve - Catskill Centre are worthwhile additions to your itinerary.

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Treat yourself

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Check prices for these dates

Our top choices for Round Top cottages

1. Warm cozy country cottage nestled beneath the mountains, woodstove, Catskill

2. Cozy 2-bedroom cottage in enchanting Catskill Mountains

3. Charming Cottage in the Heart of Catskill & Pet Friendly

4. Charming loft cottage in tranquil Germantown with WiFi, AC

5. Close to skiing in Windham and Hunter, hiking, lakes, 20+restaurants

6. Streamside Cottage Half Mile to Town of Woodstock

7. Sleepy Hollow Lake Home w/ Deck, Pool Access!

8. Boho Hot Tub Cottage | Pet-Friendly | Hudson Valley

9. Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream

10. Pet Friendly • Fenced Yard • Hot Tub • Romantic

11. Mtn-view Retreat in Huson Valley: Great for Groups

12. 'the Mountain House:' Windham Retreat w/ Hot Tub!

Find holiday rentals that suit your style

Top Round Top Hotel Reviews

Pocketbook Hotel and Bath

Hotel Vienna

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Wylder Hotel Windham

St. Charles Hotel

voco James Newbury Hudson Valley by IHG

Courtyard by Marriott Kingston

Residence Inn by Marriott Kingston

Hampton Inn Kingston

Find out more about Round Top

Round Top Cottages information

Frequently asked questions

Explore a world of travel with Expedia

Search Round Top Cottage Accommodations

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Round Top cottages

1. Warm cozy country cottage nestled beneath the mountains, woodstove, Catskill

2. Cozy 2-bedroom cottage in enchanting Catskill Mountains

3. Charming Cottage in the Heart of Catskill & Pet Friendly

4. Charming loft cottage in tranquil Germantown with WiFi, AC

5. Close to skiing in Windham and Hunter, hiking, lakes, 20+restaurants

6. Streamside Cottage Half Mile to Town of Woodstock

7. Sleepy Hollow Lake Home w/ Deck, Pool Access!

8. Boho Hot Tub Cottage | Pet-Friendly | Hudson Valley

9. Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream

10. Pet Friendly • Fenced Yard • Hot Tub • Romantic

11. Mtn-view Retreat in Huson Valley: Great for Groups

12. 'the Mountain House:' Windham Retreat w/ Hot Tub!

Find holiday rentals that suit your style

Top Round Top Hotel Reviews

Pocketbook Hotel and Bath

Find out more about Round Top

Round Top Cottages information

Frequently asked questions

Explore a world of travel with Expedia