Photo by Joe Vickiana

Holiday Rentals in Southfields

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks

Holiday Rentals in Southfields

Summer Castle: Pool, Game Room, BBQ - Pet Friendly

8.0 out of 10, Very good, (3)
"We booked the property because our family is growing too large for all of the children and grandchildren to spend the holidays together. The “holiday house” as our 4 year old coined it was the perfect place to spend Christmas and Hanukkah. Large yet cozy and very well appointed. All of our communication with proprietors was prompt and helpful, and they had the driveway salted and plowed within hours of the (very picturesque) snowfall the day before Christmas. I would happily book here again. "
The price is €1,020
includes taxes & fees
9 Jul - 10 Jul
Summer Castle: Pool, Game Room, BBQ - Pet Friendly

Contemporary Cozy Cottage

10.0 out of 10, Exceptional, (23)
"Our stay was lovely. Nadia was a wonderful host and the property was so welcoming."
The price is €365
includes taxes & fees
6 Jul - 7 Jul
Contemporary Cozy Cottage

Gorgeous Garrison Gem Pool Sauna Hot Tub More

2.0 star property
Gorgeous Garrison Gem Pool Sauna Hot Tub More

West Point Family Retreat, 5 min walk to Thayer!

2.0 star property
10.0 out of 10, Exceptional, (4)
"Nice houseAwesome kitchen Granddaughter loved the bunk bed and the many games"
The price is €720
includes taxes & fees
6 Jul - 7 Jul
West Point Family Retreat, 5 min walk to Thayer!

Lovely 3BR Home with parking-Walk to WP Gate!

10.0 out of 10, Exceptional, (4)
"Easy booking, arrival, and departure. Very nice home. Very Clean and comfortable. Host was very kind and clear on everything for stay. Will book again!"
The price is €309
includes taxes & fees
28 Jul - 29 Jul
Lovely 3BR Home with parking-Walk to WP Gate!

Fabulous 3bdrm Home w/parking!

6.0 out of 10, (1)
"The proximity to Westpoint was great. Trashy neighborhood. Very loud construction early in the morning. The cooking supplies were limited and one of the handles on the pans fell off while we were there. It was okay, but probably wouldn't return."
The price is €312
includes taxes & fees
4 Aug - 5 Aug
Fabulous 3bdrm Home w/parking!

Room for Everyone: Spacious 6BR West Point Retreat

10.0 out of 10, Exceptional, (1)
"Great location for Westpoint visit. As described. Clean with new updates. "
The price is €980
includes taxes & fees
17 Jul - 18 Jul
Room for Everyone: Spacious 6BR West Point Retreat

Aspen In Airmont NY

10.0 out of 10, Exceptional, (6)
"We had an excellent stay in this beautiful house. Favorite thing is the magnificent dining table."
The price is €1,027
includes taxes & fees
6 Jul - 7 Jul
Aspen In Airmont NY

Large, Cozy, Bright Business Class Corporate Retreat

9.0 out of 10, Wonderful, (13)
"Very cozy stay with responsive host"
The price is €593
includes taxes & fees
6 Jul - 7 Jul
Large, Cozy, Bright Business Class Corporate Retreat

Charming large Victorian in historic Newburgh

10.0 out of 10, Exceptional, (1)
The price is €863
includes taxes & fees
7 Jul - 8 Jul
Charming large Victorian in historic Newburgh

Woodland Sanctuary - 6000ft retreat for pure relaxation!

The price is €2,346
includes taxes & fees
10 Jul - 11 Jul
Woodland Sanctuary - 6000ft retreat for pure relaxation!

Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views

10.0 out of 10, Exceptional, (298)
"Beautiful, quiet property that was a great getaway from the city. A pair of bald eagles were circling the lake which was a really amazing surprise! "
The price is €468
includes taxes & fees
7 Jul - 8 Jul
Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views

5BR Home with Sauna & Pool Hot tub Fire pit

5BR Home with Sauna & Pool Hot tub Fire pit

Indoor Pool Paradise | 6BR + Huge Decks

The price is €1,214
includes taxes & fees
7 Jul - 8 Jul
Indoor Pool Paradise | 6BR + Huge Decks

The Perfect Essential Getaway!

9.6 out of 10, Exceptional, (5)
"Owner was very responsive and accommodating on the app when I had questions. Place was great."
The price is €1,125
includes taxes & fees
7 Jul - 8 Jul
The Perfect Essential Getaway!

Amazing Home Near West Point, Shopping, Skiing and Legoland

10.0 out of 10, Exceptional, (12)
"Very nice property in a nice neighborhood . Had all the amenities we needed and Ruth was super responsive. If we are in the area again, we will def stay at this location. "
The price is €493
includes taxes & fees
21 Jul - 22 Jul
Amazing Home Near West Point, Shopping, Skiing and Legoland

Waterfront Home with Hot Tub, Kayaks, and Fast Wifi

9.8 out of 10, Exceptional, (16)
"The house was very clean and beautiful inside. Beds were incredibly comfortable, short distance to town and skiing at Mt Peter which was the reason for our visit. Spa was clean although we didn’t use it because there was a snow storm. Overall great visit!"
The price is €504
includes taxes & fees
14 Jul - 15 Jul
Waterfront Home with Hot Tub, Kayaks, and Fast Wifi

Charming 3-BR house: Lake Views, Firepit, Ping Pong, & Kayaks in Greenwood Lake

10.0 out of 10, Exceptional, (1)
"The location was fantastic and the place was amazing. Our family enjoyed the great views and the house had all the amenities to spend a relaxing vacation. "
Charming 3-BR house: Lake Views, Firepit, Ping Pong, & Kayaks in Greenwood Lake

Lakeview House ~ Hot Tub ~ Firepit ~ Stunning View ~ Spacious Deck ~ Living Room

10.0 out of 10, Exceptional, (1)
"We had an amazing stay at this beautiful home! The views overlooking the lake and mountains are absolutely breathtaking—better than I could have imagined. The house itself is gorgeous, well-maintained, and equipped with everything needed for a comfortable stay. On top of that, the host was incredibly responsive and made sure everything was perfect. If you’re looking for a peaceful retreat with unbeatable scenery and top-notch hospitality, this is the place to be. I can't wait to return!"
Lakeview House ~ Hot Tub ~ Firepit ~ Stunning View ~ Spacious Deck ~ Living Room

Secluded Stunning Lake View Villa w Heated Pool, Fenced Yard & Hot Tub

9.8 out of 10, Exceptional, (8)
"Incredible place, scenic views, newly renovated house me and my family enjoyed it all! Besides that the host was very responsive and friendly."
The price is €1,503
includes taxes & fees
7 Jul - 8 Jul
Secluded Stunning Lake View Villa w Heated Pool, Fenced Yard & Hot Tub
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.
Save an average of 15% on thousands of hotels when you're signed in

Frequently asked questions

Can I find holiday rentals in Southfields?

Yes, we have holiday rentals where you'll be just 11.3 mi (18.1 km) from LEGOLAND® New York, providing a secluded option to escape the hustle and bustle.

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

Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views: This holiday home rental outside of Southfields is located on a lake, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

What can I see and do in Southfields?

Explore the area and family-friendly sights such as LEGOLAND® New York, or get out into nature at a spot like Sterling Forest State Park. Harriman State Park and Woodbury Common Premium Outlets are a couple of places you'll find in the wider area.

What are holiday rentals like in Southfields?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Southfields. Holiday rentals offer extras like kitchens and laundry facilities so you'll have a home away from home. If you're concerned about a sanitised environment, a holiday rental can provide a sense of security away from public hotel lifts and lobbies bustling with people while still allowing you to travel. You'll also find more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is an attractive option for families.