Surprise Vacation Rentals

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Check prices for these dates

Tonight
Dec 12 - Dec 13
Tomorrow
Dec 13 - Dec 14
This weekend
Dec 12 - Dec 14
Next weekend
Dec 19 - Dec 21

Our top choices for Surprise vacation rentals

Mini-fridge, stovetop, cookware/dishes/utensils, paper towels
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Cabin in Catskill

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
2.0 star property
9.6 out of 10, Exceptional, (107)
"The hospitality and making sure our stay was enjoyable most of all our needs during the time being. "
United States
Yessica
The price is ￥18,503
￥26,701 total
includes taxes & fees
Dec 14 - Dec 15
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
Balcony
Micosta Leisure Inn

Aparthotel in Hudson

Micosta Leisure Inn
3.0 star property
9.2 out of 10, Wonderful, (132)
"Clean, pet friendly , just an overall super nice place to stay "
United States
Gail
The price is ￥20,204
￥22,630 total
includes taxes & fees
Dec 14 - Dec 15
Micosta Leisure Inn
Exterior
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY

Cabin in Saugerties

'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
8.2 out of 10, Very Good, (46)
"We had an amazing peaceful time at this property. Check in was seamless and we got lots of great recommendations from our hosts that we really enjoyed! It was very private and cozy and really helped us relax and renew! We will definitely be returning. "
United States
Josh M.
The price is ￥19,436
￥25,251 total
includes taxes & fees
Dec 17 - Dec 18
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
Exterior
A Spectacular 50 Mile View of the Hudson Valley in all seasons

Apartment in Saugerties

A Spectacular 50 Mile View of the Hudson Valley in all seasons
9.8 out of 10, Exceptional, (95)
"Enjoyed our stay!"
United States
Mike T.
A Spectacular 50 Mile View of the Hudson Valley in all seasons
Exterior
THE LUXURY LODGE - SKI, RIDE, GOLF, BIKE, HIKE

Cabin in Hunter

THE LUXURY LODGE - SKI, RIDE, GOLF, BIKE, HIKE
10.0 out of 10, Exceptional, (271)
"House was great. Plenty of beds, great kitchen and large table for all. Kitchen was well stocked. "
United States
Sarah A.
The price is ￥62,324
￥151,952 total
includes taxes & fees
Dec 15 - Dec 16
THE LUXURY LODGE - SKI, RIDE, GOLF, BIKE, HIKE
Outdoor dining
A'Neils Windham Ski Lodge & Family Retreat

Vacation Home in Windham

A'Neils Windham Ski Lodge & Family Retreat
9.8 out of 10, Exceptional, (31)
"Excellent! The host was super friendly, helpful and was an excellent communicator. We had a great time!"
United States
Ray L.
A'Neils Windham Ski Lodge & Family Retreat
Exterior
Cozy Catskill Cabin w/ 10-minute Walk to Downtown Catskill

Cabin in Catskill

Cozy Catskill Cabin w/ 10-minute Walk to Downtown Catskill
9.8 out of 10, Exceptional, (33)
"Very nice cabin lots of property space "
United States
Martin Z.
The price is ￥23,370
￥51,268 total
includes taxes & fees
Dec 18 - Dec 19
Cozy Catskill Cabin w/ 10-minute Walk to Downtown Catskill
Fridge, microwave, oven, stovetop
LOCATION! Location! Walking distance to Hunter MT! FALL 3rd nt SPECIAL!

Vacation Home in Hunter

LOCATION! Location! Walking distance to Hunter MT! FALL 3rd nt SPECIAL!
9.6 out of 10, Exceptional, (51)
"Comfortable stay with plenty of room and very close to Hunter Mountain for skiing. Views of the slopes from the hot tub were fantastic "
United States
Chris S.
LOCATION! Location! Walking distance to Hunter MT! FALL 3rd nt SPECIAL!
Exterior
Beautiful new house 3/4 mile from Hunter Mountain

Vacation Home in hunter

Beautiful new house 3/4 mile from Hunter Mountain
9.6 out of 10, Exceptional, (138)
"Really beautiful location with plenty of bedrooms. Very clean!"
United States
Ellen B.
Beautiful new house 3/4 mile from Hunter Mountain
Outdoor dining
Private Pickleball Ct - Indoor Hot Tub - Spa Room - Lift Tkts

Vacation Home in Windham

Private Pickleball Ct - Indoor Hot Tub - Spa Room - Lift Tkts
10.0 out of 10, Exceptional, (105)
"Rick has an incredible property to share and is a gracious host. A sure place to spend time with friends and family - cant wait to come back again."
United States
Chris R.
Private Pickleball Ct - Indoor Hot Tub - Spa Room - Lift Tkts
Exterior
LOCATION! LOCATION!LOCATION! Luxurious Ski In/Out Jet-Set Condo NEWLY RENOVATED

Condo in Hunter Highlands

LOCATION! LOCATION!LOCATION! Luxurious Ski In/Out Jet-Set Condo NEWLY RENOVATED
10.0 out of 10, Exceptional, (10)
"We loved staying at this condo. The location was amazing for back and forth to the slopes it was so easy! The beds were so comfortable and the house was clean! Communication with the owner was excellent. We will definitely stay again! "
United States
Melissa B.
The price is ￥125,410
￥202,614 total
includes taxes & fees
Dec 15 - Dec 16
LOCATION! LOCATION!LOCATION! Luxurious Ski In/Out Jet-Set Condo NEWLY RENOVATED
Terrace/patio
Sleeps 27/Pickleball Court/Game Room/Hot Tub/Pool/Batting Cage/Beach

Vacation Home in Coxsackie

Sleeps 27/Pickleball Court/Game Room/Hot Tub/Pool/Batting Cage/Beach
10.0 out of 10, Exceptional, (168)
"Had an absolutely amazing time here! Jody was very prompt with responding to any questions we had during the duration of our stay. The house was so perfect. 5 Stars!!"
United States
Steve B.
Sleeps 27/Pickleball Court/Game Room/Hot Tub/Pool/Batting Cage/Beach
Exterior
Beautiful 5-star Estate! Pool, Pond, Game Room, Gym, Library, Party Barn, Trails

Vacation Home in Old Chatham

Beautiful 5-star Estate! Pool, Pond, Game Room, Gym, Library, Party Barn, Trails
9.6 out of 10, Exceptional, (93)
"What a lovely property. Laurie was so kind and helpful checking us in, and the house was so fun. Would absolutely stay here again. "
United States
Daniel R.
Beautiful 5-star Estate! Pool, Pond, Game Room, Gym, Library, Party Barn, Trails
Property grounds
Private Yacht on Catskill Creek

Houseboat in Catskill

Private Yacht on Catskill Creek
9.8 out of 10, Exceptional, (28)
"It is a fun alternative to conventional hotel/motel stays. Beautiful waking up on Catskill Creek with as much room as a small hotel room, including 2 double beds plus a dining table that can convert to a bed."
United States
Jay
Private Yacht on Catskill Creek
Exterior
Modern Luxurious Cabin, Catskills - The Tiny Nook

Vacation Home in Catskill

Modern Luxurious Cabin, Catskills - The Tiny Nook
10.0 out of 10, Exceptional, (7)
"Great place. Exactly like the pictures. "
United States
robert a.
The price is ￥24,878
￥51,554 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Modern Luxurious Cabin, Catskills - The Tiny Nook
Property grounds
Magical Home Located in Windham and Catskills

Vacation Home in Windham

Magical Home Located in Windham and Catskills
2.0 star property
10.0 out of 10, Exceptional, (12)
"Nice cozy home"
United States
Romonia F.
Magical Home Located in Windham and Catskills
Exterior
Sioux Tipi on Chloe's Lake

Vacation Home in Saugerties

Sioux Tipi on Chloe's Lake
9.8 out of 10, Exceptional, (6)
"This was such a cool experience Id love to go back! "
United States
Brandon
Sioux Tipi on Chloe's Lake
Interior
6BR/7bath Luxury home Hot Tub in Hunter Catskills

Vacation Home in Hunter

6BR/7bath Luxury home Hot Tub in Hunter Catskills
9.6 out of 10, Exceptional, (4)
"The property wa everything we imaged. The host was great and very responsive. My family enjoyed the 2nd floor space just as much as the fire out in the back years. The scenery was awesome! "
United States
Sheena C.
6BR/7bath Luxury home Hot Tub in Hunter Catskills
Smart TV, fireplace, computer monitors
SPECTACULAR Hunter Mountain Views, INCREDIBLE LOCATION-2 minutes to slopes !!

Vacation Home in Hunter

SPECTACULAR Hunter Mountain Views, INCREDIBLE LOCATION-2 minutes to slopes !!
9.6 out of 10, Exceptional, (31)
"Great stay in a great location. Mountain View with the fire pit was amazing! "
United States
Conor D.
SPECTACULAR Hunter Mountain Views, INCREDIBLE LOCATION-2 minutes to slopes !!
Terrace/patio
Heart of Hunter Village; across MT!FaLL Special3rd nt half OFF!”wknd stay

Vacation Home in Hunter

Heart of Hunter Village; across MT!FaLL Special3rd nt half OFF!”wknd stay
9.6 out of 10, Exceptional, (77)
"House was very clean. Property managers were very responsive to check in and check out time and anything we needed during our stay. Very close to the mountain and beautiful location. Would highly recommend."
United States
Jamie M.
Heart of Hunter Village; across MT!FaLL Special3rd nt half OFF!”wknd stay
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 Surprise Hotel Reviews

Pocketbook Hotel and Bath

Pocketbook Hotel and Bath

10/10 Excellent
"This was a very cool new hotel. Easy walk into the cute town of Hudson. They are still working out some kinks, we didn’t have hot water but staff was very understanding and offered us "
Lisa 1-night trip
Posted 4 days ago
Pocketbook Hotel and Bath

Find out more about Surprise

Search for holiday rentals in Surprise on Expedia! You can easily find your home rentals, villas, holiday apartments in Surprise 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 Surprise!

Frequently asked questions

Can I find a vacation rental in Surprise?

Yes, there are vacation rentals near top local attractions in Surprise, or you can go with a more remote option if you're looking for relaxation.

What are some of the best vacation home rentals that Surprise has to offer?

Best rated cabin in Hunter cozy 4 Bedrooms 3 full baths Sauna great location: This vacation home rental outside of Surprise is located on the waterfront and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of games.

What can I see and do in Surprise?

Explore the area and family-friendly sights such as Zoom Flume, or get out into nature at a spot like Sleepy Hollow Lake. Catskill Golf Club and Thomas Cole National Historic Site are a couple of places you'll find in the larger area.

What are vacation rentals like in Surprise?

Vacation rentals are privately owned accommodations you can stay in for a short or long stay in Surprise. Vacation rentals provide amenities such as hot tubs, fire pits, and patios so you'll have all the conveniences of home. If you're concerned about cleanliness, vacation rentals can offer a sense of security away from shared hotel elevators and lobbies packed with people 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 a great choice for small groups.