Discover Your Perfect Upper East Side Vacation Homes

Best Vacation Homes in Upper East Side

New
850 ft² 10 Guests 3 Bedrooms 3 Bathrooms
Family Friendly Apartment
  • Fireplace/Heating
  • Kitchen
  • Air Conditioner
US $1,660/Night For 7 Nights US $11,622
10.0
Exceptional
(2 Reviews)
215.28 ft² 2 Guests 1 Bedroom 1 Bathroom
Free Cancellation House
  • Fireplace/Heating
  • Internet
  • Security/Safety
US $284/Night For 7 Nights US $1,991
9.2
Exceptional
(902 Reviews)
1 Bathroom
Couples Retreat Hotel
  • Parking
  • Air Conditioner
  • Internet
US $312/Night For 7 Nights US $2,182
New
6 Guests 3 Bedrooms 1 Bathroom
Family Friendly Apartment
  • Fireplace/Heating
  • Balcony/Terrace
  • Kitchen
US $1,650/Night For 7 Nights US $11,549
10.0
Exceptional
(1 Review)
1011.81 ft² 6 Guests 3 Bedrooms 2 Bathrooms
Apartment
  • Fireplace/Heating
  • Air Conditioner
  • Internet
US $1,126/Night For 7 Nights US $7,884
New
8 Guests 3 Bedrooms 2 Bathrooms
Family Friendly Apartment
  • Fireplace/Heating
  • Kitchen
  • Air Conditioner
US $519/Night For 7 Nights US $3,631
New
700 ft² 4 Guests 2 Bedrooms 1 Bathroom
Family Friendly Apartment
  • Fireplace/Heating
  • Pet Friendly
  • Kitchen
US $254/Night For 7 Nights US $1,780
New
350 ft² 2 Guests 1 Bedroom 1 Bathroom
Family Friendly Apartment
  • Fireplace/Heating
  • Pet Friendly
  • Kitchen
US $201/Night For 7 Nights US $1,406

Upper East Side Luxury Rentals

New
6 Guests 3 Bedrooms 2 Bathrooms
Family Friendly Apartment
  • Kitchen
  • Air Conditioner
  • Internet
US $2,759/Night For 7 Nights US $19,310
New
13 Guests 7 Bedrooms 7 Bathrooms
Family Friendly House
  • Hot Tub
  • Fireplace/Heating
  • Balcony/Terrace
US $2,609/Night For 7 Nights US $18,263
9.2
Exceptional
(6 Reviews)
6501.4 ft² 13 Guests 7 Bedrooms 7 Bathrooms
Villa
  • Hot Tub
  • Fireplace/Heating
  • Balcony/Terrace
US $2,250/Night For 7 Nights US $15,750
New
1200 ft² 10 Guests 3 Bedrooms 3 Bathrooms
Family Friendly Apartment
  • Fireplace/Heating
  • Kitchen
  • Air Conditioner
US $2,053/Night For 7 Nights US $14,369
9.7
Exceptional
(9 Reviews)
1194.79 ft² 10 Guests 3 Bedrooms 3 Bathrooms
Free Cancellation Apartment
  • Air Conditioner
  • Internet
  • Child Friendly
US $1,998/Night For 7 Nights US $13,983
New
2255 ft² 10 Guests 4 Bedrooms 3 Bathrooms
Family Friendly Apartment
  • Fireplace/Heating
  • Pool
  • Balcony/Terrace
US $1,919/Night For 7 Nights US $13,430
10.0
Exceptional
(5 Reviews)
8 Guests 3 Bedrooms 2 Bathrooms
Family Friendly Apartment
  • Fireplace/Heating
  • Balcony/Terrace
  • Kitchen
US $1,829/Night For 7 Nights US $12,801
8.6
Fabulous
(20 Reviews)
7 Guests 3 Bedrooms 1 Bathroom
Family Friendly Apartment
  • Fireplace/Heating
  • Balcony/Terrace
  • Kitchen
US $1,668/Night For 7 Nights US $11,679

Upper East Side Pet Friendly Vacation Rentals

10.0
Exceptional
(2 Reviews)
700 ft² 2 Guests 2 Bedrooms 1 Bathroom
Family Friendly Apartment
  • Fireplace/Heating
  • Pet Friendly
  • Kitchen
US $549/Night For 7 Nights US $3,844
10.0
Exceptional
(1 Review)
398.26 ft² 3 Guests 1 Bedroom 1 Bathroom
Apartment
  • Fireplace/Heating
  • Pet Friendly
  • Parking
US $370/Night For 7 Nights US $2,590
New
5 Guests 2 Bedrooms 2 Bathrooms
Family Friendly Apartment
  • Fireplace/Heating
  • Balcony/Terrace
  • Pet Friendly
US $498/Night For 7 Nights US $3,488
9.6
Exceptional
(7 Reviews)
900 ft² 4 Guests 2 Bedrooms 1 Bathroom
Family Friendly Apartment
  • Fireplace/Heating
  • Pet Friendly
  • Kitchen
US $570/Night For 7 Nights US $3,992
10.0
Exceptional
(1 Review)
398.26 ft² 3 Guests 1 Bedroom 1 Bathroom
Pet Friendly Apartment
  • Fireplace/Heating
  • Pet Friendly
  • Parking
US $333/Night For 7 Nights US $2,331
9.4
Exceptional
(9 Reviews)
6 Guests 2 Bedrooms 2 Bathrooms
Family Friendly Apartment
  • Fireplace/Heating
  • Balcony/Terrace
  • Pet Friendly
US $910/Night For 7 Nights US $6,368
9.2
Exceptional
(20 Reviews)
2 Guests 1 Bedroom 1 Bathroom
Family Friendly Apartment
  • Fireplace/Heating
  • Balcony/Terrace
  • Pet Friendly
US $528/Night For 7 Nights US $3,693
8.8
Fabulous
(6 Reviews)
6 Guests 2 Bedrooms 2 Bathrooms
Family Friendly Apartment
  • Fireplace/Heating
  • Pet Friendly
  • Kitchen
US $1,416/Night For 7 Nights US $9,911

Upper East Side Large Vacation Homes

New
1900 ft² 10 Guests 5 Bedrooms 3 Bathrooms
Family Friendly House
  • Fireplace/Heating
  • Balcony/Terrace
  • Pet Friendly
US $550/Night For 7 Nights US $3,848
9.2
Exceptional
(7 Reviews)
452.09 ft² 6 Guests 10 Bedrooms 2 Bathrooms
Apartment
  • Fireplace/Heating
  • Air Conditioner
  • Internet
US $94/Night For 7 Nights US $658
New
4060 ft² 15 Guests 6 Bedrooms 4 Bathrooms
Group Friendly House
  • Private Pool
  • Hot Tub
  • Pool
US $1,000/Night For 7 Nights US $7,000
8.0
Excellent
(1 Review)
37 Guests 7 Bedrooms 7 Bathrooms
Family Friendly Apartment
  • Air Conditioner
  • Internet
  • Child Friendly
US $293/Night For 7 Nights US $2,048
10.0
Exceptional
(3 Reviews)
4800 ft² 14 Guests 6 Bedrooms 4 Bathrooms
Family Friendly House
  • Fireplace/Heating
  • Balcony/Terrace
  • Pet Friendly
US $1,447/Night For 7 Nights US $10,131
4.9
Average
(56 Reviews)
6000 ft² 13 Guests 7 Bedrooms 7 Bathrooms
Family Friendly Apartment
  • Child Friendly
US $2,150/Night For 7 Nights US $15,050
New
8 Guests 6 Bedrooms 5 Bathrooms
Family Friendly House
  • Balcony/Terrace
  • Kitchen
  • Air Conditioner
US $2,500/Night For 7 Nights US $17,500
New
30 Guests 1 Bedroom 1 Bathroom
Family Friendly Apartment
  • Fireplace/Heating
  • Kitchen
  • Parking
US $179/Night For 7 Nights US $1,253

Why Choose Rent By Owner for your Upper East Side Vacation Rental Homes?

What makes our Vacation Rentals special?

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Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
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Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Best Times to Visit Upper East Side

When should you plan your Vacation Rentals stay?

Choosing the right time to visit the area can enhance your experience, as seasonal variations influence the local atmosphere and availability of vacation rentals here in the Upper East Side, New York.

Peak Season Highlights

spring
Spring (March to May)

During spring, the area experiences mild weather and vibrant city events, making it an ideal time to explore this destination’s cultural scene comfortably.

Average Temperature Daytime: 60-70°F - Nighttime: 45-55°F
autumn
Fall (September to November)

Fall offers pleasant temperatures and fewer crowds, allowing you to enjoy the neighborhood’s sophisticated atmosphere at a more relaxed pace.

Average Temperature Daytime: 65-75°F - Nighttime: 50-60°F

Off-Season Highlights

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Summer (June to August)

In summer, the region experiences warmer weather and lively outdoor activities, perfect for those who enjoy a bustling urban environment.

Average Temperature Daytime: 75-85°F - Nighttime: 65-70°F
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Winter (December to February)

Winter brings colder temperatures and a quieter ambiance, offering a peaceful setting to appreciate the elegant architecture and nearby attractions.

Average Temperature Daytime: 30-40°F - Nighttime: 20-30°F

Weekly Weather Forecast for Upper East Side

Booking Steps

01

Search Properties

Use our filters to find the right property that fits your needs.
02

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.
03

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Indoor Features

  • Fully-equipped kitchens with modern appliances
  • Comfortable living areas with flat-screen TVs
  • Free Wi-Fi for staying connected
  • Air conditioning and heating for year-round comfort
  • In-unit washers and dryers for convenience
  • Luxurious bedrooms with premium bedding
  • Spa-like bathrooms with soaking tubs or walk-in showers

Outdoor Amenities

  • Enjoy access to a private outdoor patio or rooftop terrace for relaxing and entertaining.
  • Take advantage of beautifully landscaped gardens or courtyards shared with other guests.
  • Make use of outdoor seating areas equipped with tables and chairs for al fresco dining.
  • Benefit from nearby parks and green spaces ideal for jogging, picnicking, or leisurely walks.
  • Experience the convenience of on-site bike racks or storage for exploring the city on two wheels.
  • Participate in outdoor fitness or wellness activities organized within communal outdoor spaces.
  • Capitalize on scenic views of the city skyline from outdoor balconies or terraces.
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Family Activities

  • Visit the Guggenheim Museum: Explore world-class modern art collections in this iconic museum, perfect for engaging the whole family in cultural discovery.
  • Stroll through Central Park's East Side entrances: Enjoy outdoor activities and playgrounds in this expansive urban oasis located right nearby, offering a refreshing break from city sightseeing.
  • Discover the Children's Museum of the Arts: Immerse your kids in creative workshops and interactive exhibits designed to inspire young imaginations within the neighborhood.
  • Participate in guided architecture tours: Learn about the area's historic buildings and skyscrapers with family-friendly tours that bring the local skyline to life.
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Adult Activities

  • Visit the Metropolitan Museum of Art: Explore world-renowned art collections and immersive exhibitions to enrich your cultural experience in this iconic destination.
  • Stroll through Central Park's Upper East Side areas: Enjoy leisurely walks along scenic paths, relax in lush green spaces, and discover charming landmarks right in the heart of the region.
  • Attend a performance at the New York City Ballet or nearby theaters: Experience world-class performances that highlight the vibrant arts scene of this established arts district.
  • Explore boutique shopping along Madison Avenue: Discover high-end stores and unique shops offering an elegant shopping experience within this upscale neighborhood.

Upper East Side Travel Tips

How Can You Make the Most of Your Stay?

  • Explore local attractions early: Take advantage of the region’s cultural offerings by planning your visits during off-peak hours to enjoy a more relaxed experience.
  • Choose well-located vacation rentals: Opt for properties near major transit lines and amenities to maximize convenience and immersion in the area's vibrant neighborhood life.
  • Embrace nearby culinary delights: Sample authentic regional cuisine at local cafes and restaurants, making your stay here even more memorable.
  • Plan your days strategically: Organize your sightseeing to include iconic spots within walking distance, ensuring you make the most of your time in this destination.

Transportation Options

  • Subway Services: The extensive subway network offers quick and reliable connections across the city, making it easy to explore beyond the neighborhood.
  • Bus Transit: Numerous local bus routes provide convenient access within the area and to other parts of the city, ideal for flexible travel options.
  • Citi Bike Rentals: Public bike-sharing stations are available nearby, allowing you to enjoy scenic rides through the city at your own pace.
  • Taxis and Ride-Sharing: Taxis and ride-sharing services like Uber and Lyft operate frequently in the region, offering comfortable door-to-door transportation.

Local Customs Options

  • Respect for Quiet Hours: Maintaining a peaceful atmosphere, especially in residential areas, is highly valued here and observed through considerate noise levels during late evening hours.
  • Holiday Celebrations: Participating in local traditions such as Labor Day parades and holiday gatherings reflects the community's pride and festive spirit in this region.
  • Dining Etiquette: When frequenting neighborhood eateries, it’s customary to be punctual and courteous, respecting the diverse culinary customs that thrive here.
  • Environmental Awareness: Recycling and eco-friendly practices are embraced locally, encouraging responsible living amidst the city’s vibrant urban environment.

Upper East Side Vacation Rental Frequently Asked Questions

2. Which vacation homes in Upper East Side are best for families?

If you are looking for a family-friendly vacation home in Upper East Side, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Upper East Side:

3. How many Rentbyowner vacation rentals are available in Upper East Side?

Currently, the total number of properties listed by Rent By Owner in 2026 is over 963 in the Upper East Side area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Upper East Side. 

4. What is the cancellation policy for vacation rentals in this area?

Cancellation policies vary by listing, so it is important to review the specific property's terms before booking. You can find detailed information on each listing page or contact the host directly for clarification.

5. How do I confirm my reservation and what are the payment options?

Reservations are confirmed through the listing platform with secure payment options. Details about accepted payment methods and confirmation procedures will be provided during the booking process or upon contacting the property owner.

6. Are there any additional fees or deposits required when booking in this destination?

Additional fees such as cleaning or security deposits are common and typically outlined in the listing details. Make sure to review all charges before completing your booking or reach out to the host for clarification.

7. What amenities are typically available in vacation rentals here?

Most properties offer essential amenities like Wi-Fi, kitchen facilities, and air conditioning. For specific features or luxury extras, refer to the individual listing descriptions or contact the host directly.

8. What should I know about the check-in and check-out procedures in the region?

Check-in and check-out times are specified in each listing. Some hosts may offer flexible arrangements; others follow standard procedures. Contact the property owner beforehand to confirm details and ensure a smooth arrival and departure.

Upper East Side Top Rated Vacation Rentals

10.0
Exceptional
(34 Reviews)
1550 ft² 4 Guests 2 Bedrooms 2 Bathrooms
Family Friendly Apartment
  • Private Pool
  • Fireplace/Heating
  • Pool
US $751/Night For 7 Nights US $5,254
New
5 Guests 2 Bedrooms 2 Bathrooms
Pet Friendly Condo
  • Pool
  • Pet Friendly
  • Air Conditioner
US $1,097/Night For 7 Nights US $7,676
New
1295 ft² 5 Guests 2 Bedrooms 2 Bathrooms
Family Friendly Apartment
  • Spa
  • Fireplace/Heating
  • Pool
US $621/Night For 7 Nights US $4,345
New
1594 ft² 4 Guests 2 Bedrooms 2 Bathrooms
Family Friendly Condo
  • Fireplace/Heating
  • Pool
  • Kitchen
US $592/Night For 7 Nights US $4,141
New
900 ft² 4 Guests 2 Bedrooms 2 Bathrooms
Family Friendly Apartment
  • Fireplace/Heating
  • Pool
  • Pet Friendly
US $404/Night For 7 Nights US $2,828
New
756 ft² 2 Guests 1 Bedroom 1 Bathroom
Family Friendly Apartment
  • Fireplace/Heating
  • Pool
  • Pet Friendly
US $348/Night For 7 Nights US $2,436
New
480 ft² 2 Guests 1 Bedroom 1 Bathroom
Family Friendly Apartment
  • Fireplace/Heating
  • Pool
  • Pet Friendly
US $252/Night For 7 Nights US $1,762
5.0
Average
(1 Review)
4 Guests 2 Bedrooms 2 Bathrooms
Family Friendly Apartment
  • Pool
  • Pet Friendly
  • Kitchen
US $293/Night For 7 Nights US $2,051