Windham Oceanfront Vacation Rentals
House
10.0(7 Reviews)
1 Bedroom
1 Bath
4 Guests
1 ft²
Fireplace/Heating
Ocean View
Balcony/Terrace
View
US $131/Night
7 Nights - US $920
House
10.0(1 Review)
3 Bedrooms
2 Baths
6 Guests
1797.57 ft²
Oceanfront- Fireplace/Heating
- Ocean View
- View
US $409/Night
7 Nights - US $2,865
Bed & Breakfast
9.0(28 Reviews)
1 Bedroom
1 Bath
Spa
Skiing- Fireplace/Heating
- Ocean View
US $247/Night
7 Nights - US $1,731
Apartment
10.0(6 Reviews)
2 Bedrooms
2 Baths
4 Guests
1 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $215/Night
7 Nights - US $1,504
House
9.0(1 Review)
5 Bedrooms
4 Baths
16 Guests
3304.52 ft²
Private Pool- Oceanfront
Pool- Ocean View
US $1,336/Night
7 Nights - US $9,350
House
10.0(110 Reviews)
6 Bedrooms
3 Baths
14 Guests
4200 ft²
Hot Tub- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $1,205/Night
7 Nights - US $8,435
Villa
8 Bedrooms
4 Baths
17 Guests
6996.54 ft²
- Oceanfront
- Hot Tub
- Skiing
- Fireplace/Heating
US $1,299/Night
7 Nights - US $9,093
House
10.0(66 Reviews)
4 Bedrooms
3 Baths
8 Guests
2784 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $503/Night
7 Nights - US $3,523
US $159/Night
7 Nights - US $1,113
House
10.0(62 Reviews)
5 Bedrooms
2 Baths
8 Guests
2028 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Ocean View
US $360/Night
7 Nights - US $2,520
US $357/Night
7 Nights - US $2,499
House
10.0(42 Reviews)
3 Bedrooms
2 Baths
6 Guests
1750 ft²
- Hot Tub
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $300/Night
7 Nights - US $2,100
Why Choose Rent By Owner for your Windham Oceanfront Vacation Rentals?
What makes our Oceanfront Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Best Times to Visit Windham
When should you plan your Oceanfront Vacation Rentals stay?
Choosing the right time to visit here ensures you can enjoy the area's natural beauty and outdoor activities at their best, making your oceanfront rental experience in Windham, New York, truly memorable and well-suited to your preferences.
Peak Season Highlights
Summer (June to August)
During the warm summer months, visitors flock to the area for outdoor activities and scenic views, making it an ideal time to secure oceanfront rentals with stunning water vistas.
Average Temperature Daytime: 75°F to 85°F - Nighttime: 55°F to 65°F
Fall (September to November)
The vibrant foliage and crisp air attract travelers seeking a peaceful retreat in this destination's scenic surroundings, perfect for booking oceanfront rentals that offer tranquility and natural beauty.
Average Temperature Daytime: 60°F to 70°F - Nighttime: 40°F to 50°F
Off-Season Highlights
Early Spring (March to April)
As the region transitions from winter, fewer visitors arrive, offering a quieter experience and a chance to enjoy the serene oceanfront settings at a more relaxed pace.
Average Temperature Daytime: 45°F to 55°F - Nighttime: 30°F to 40°F
Late Winter (January to February)
During this period, the area experiences its quietest phase, making it an excellent opportunity for those seeking solitude in cozy oceanfront accommodations away from the crowds.
Average Temperature Daytime: 30°F to 40°F - Nighttime: 15°F to 25°F
Weekly Weather Forecast for Windham
How to Book Your Windham Oceanfront Vacation Rentals
What's our booking process?
Our platform allows you to browse a curated selection of oceanfront vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
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.
Explore and book the perfect rental in Windham
Common Oceanfront Vacation Rentals Amenities
What amenities can you expect?
Our Oceanfront Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
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 spacious outdoor seating areas perfect for relaxing and taking in scenic views of the surrounding landscape.
- Take advantage of private or shared outdoor grills to prepare delicious meals amidst the fresh air.
- Benefit from well-maintained walking trails or pathways that allow you to explore the natural beauty of the region.
- Make the most of outdoor fire pits for cozy evenings under the stars with friends and family.
- Experience the convenience of on-site parking facilities tailored for easy access to your oceanfront rental.
- Utilize outdoor recreational equipment such as bikes, kayaks, or paddleboards often available at the property.
- Admire panoramic views from private decks or patios, ideal for morning coffee or sunset watching.
Top Attractions Around Windham
What attractions are nearby?
Within this picturesque area, you can enjoy a variety of outdoor activities such as hiking, mountain biking, and scenic nature walks, all just minutes from your oceanfront rental in Windham, New York, offering an ideal setting for relaxation and adventure amidst stunning natural landscapes.
Family Activities
- Windham Mountain Resort Enjoy a family-friendly day on the slopes with skiing, snowboarding, and snow tubing during winter months, offering fun for all ages in this scenic region.
- Windham Path Take a leisurely stroll or bike ride along this trail that meanders through the area’s natural beauty, perfect for outdoor family activities and exploring the region's landscape.
- Windham Theatre Experience local culture by attending family-friendly performances and shows that bring entertainment and community spirit to this destination.
- Local Parks and Playgrounds Spend quality time outdoors at parks and playgrounds designed for children, providing safe spaces for play and relaxation in the region.
Adult Activities
- Hiking Trails Exploration: Discover scenic trails in the area that offer breathtaking views and invigorating outdoor experiences, perfect for those seeking adventure surrounded by nature.
- Local Breweries and Wineries Tour: Indulge in the region's craft beverages at local breweries and wineries, providing a relaxing way to enjoy the area's flavors and unwind from your day.
- Golfing at Nearby Courses: Tee off at well-maintained golf courses nearby, ideal for enjoying a leisurely game amidst the picturesque landscape of this destination.
- Visit Cultural and Arts Centers: Explore galleries and cultural centers that showcase regional art and history, enriching your experience in this charming locale.
Other Places to Stay in Windham, NY
Windham Mountain Resort
Windham Country Club
Windham Vineyards and Winery
Ashland
Windham Travel Tips
How Can You Make the Most of Your Stay?
- Plan Your Activities in Advance: Research local outdoor pursuits to fully enjoy the scenic beauty and recreational offerings near your oceanfront rental.
- Choose the Right Accommodation: Select an oceanfront rental that provides direct access to the water and amenities tailored for a comfortable stay in this destination.
- Explore Local Cuisine and Markets: Take advantage of nearby eateries and markets to savor regional flavors during your visit to this region.
- Respect Nature and Community Guidelines: Follow environmental practices and community rules to preserve the area's natural charm for future visitors.
Transportation Options
- Windham-Amsterdam Bus Service: This regional bus service offers convenient transportation connecting travelers to and from the area, making it easy to explore without a car.
- Local Taxi Services: A reliable option for quick, door-to-door travel within the region, ideal for reaching nearby attractions or your oceanfront rental.
- Rental Car Agencies: Numerous rental agencies are available here, providing flexibility to explore Windham and its surroundings at your own pace.
- Shuttle Services: Specialized shuttle options operate seasonally, offering direct transfers between key points and your oceanfront accommodations in the area.
Local Customs Options
- Lunar New Year Celebrations: The local community observes the Lunar New Year with traditional festivities that emphasize family gatherings and cultural displays, providing an authentic experience for visitors seeking to immerse themselves in regional customs.
- Farmers Markets: Weekly farmers’ markets showcase locally grown produce and handmade crafts, reflecting the region’s appreciation for fresh, sustainable food and artisanal products that you can enjoy during your stay.
- Seasonal Folk Festivals: Throughout the year, seasonal festivals celebrate the area's heritage through music, dance, and storytelling, offering a glimpse into this destination's rich cultural tapestry.
- Religious Observances: Traditional religious ceremonies and holiday observances are an integral part of community life here, allowing visitors to gain insight into the spiritual practices that shape local customs.
Windham Oceanfront Vacation Rentals Frequently Asked Questions
1. What are the top Oceanfront Rentals in Windham?
There are a lot of options in Windham. If you plan on staying in the Windham area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Oceanfront Rentals in Windham:
- Above & beyond. Perfect house for family, friends & fresh air.
- GREAT FOR FAMILIES! 3 MINUTE WALK TO MAIN STREET & 1 MILE FROM WINDHAM SKI MT.
- 40 acres. seasonal rental.Mountain views.sleeps 12+.perfect for 2 families.
- Windham/Hunter Mountain
- 7 Bedroom Luxurious Chalet In Windham, NY
- Chalet nestled right in Windham Mountain's quiet beauty-private access to trails
- Simply Amazing Condo
- 5 Min to Windham Mtn! Luxury Retreat w/Mountain Views! Natural Swimming Pond
- Windham and Hunter Mountain Ski House.
- Retreat mountain home
2. How many Oceanfront Rentals are available in Windham?
Currently, the total number of properties listed by RBO in 2026 is over 36 in the Windham area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Oceanfront Rentals in Windham.
3. What is the cancellation policy for oceanfront rentals in Windham, New York?
Cancellation policies vary depending on the property owner. Please review the specific rental listing for detailed information or contact the owner directly to understand your options and any applicable fees.
4. Are there any special requirements or fees when booking oceanfront accommodations in this area?
Additional requirements or fees, such as cleaning charges or security deposits, are outlined in each property’s listing. Be sure to read the details carefully or reach out to the host for clarification.
5. What amenities are typically included with oceanfront rentals in Windham?
Amenities can differ between properties but often include features like private decks, beach access, and fully equipped kitchens. Check the listing for a comprehensive list of included amenities before confirming your reservation.
6. Is there a minimum stay requirement for oceanfront rentals here?
Minimum stay requirements depend on the property owner and the time of year. Details are specified in each listing, so review these or contact the owner for specific booking restrictions.
7. How do I ensure my booking is secure when reserving an oceanfront rental in this destination?
Bookings made through trusted platforms offer secure payment options and verified listings. Always confirm that you're booking through a reputable site and communicate directly with the property owner if you have any concerns.
More Rentals You May Like Near Windham
Hotel
7.6(14 Reviews)
10 Baths
565.1 ft²
- Oceanfront
- Skiing
- Fireplace/Heating
- Pool
US $199/Night
7 Nights - US $1,393
House
10.0(28 Reviews)
5 Bedrooms
2 Baths
12 Guests
- Private Pool
- Fireplace/Heating
- Pool
- Ocean View
US $1,389/Night
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House
10.0(25 Reviews)
9 Bedrooms
7 Baths
18 Guests
10611 ft²
- Private Pool
- Hot Tub
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- Pool
US $3,873/Night
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Condo
10.0(24 Reviews)
4 Bedrooms
4 Baths
10 Guests
1812 ft²
- Hot Tub
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US $693/Night
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Ski Chalet
10.0(13 Reviews)
4 Bedrooms
3 Baths
12 Guests
3000 ft²
- Hot Tub
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $982/Night
7 Nights - US $6,877
Ski Chalet
10.0(6 Reviews)
5 Bedrooms
4 Baths
12 Guests
4000 ft²
- Hot Tub
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $1,038/Night
7 Nights - US $7,265
House
10.0(6 Reviews)
3 Bedrooms
2 Baths
6 Guests
1100 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $218/Night
7 Nights - US $1,523
Ski Chalet
10.0(5 Reviews)
3 Bedrooms
3 Baths
8 Guests
1 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $275/Night
7 Nights - US $1,927
House
10.0(4 Reviews)
5 Bedrooms
4 Baths
14 Guests
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $1,525/Night
7 Nights - US $10,672
House
10.0(4 Reviews)
5 Bedrooms
4 Baths
12 Guests
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $1,125/Night
7 Nights - US $7,875
House
10.0(3 Reviews)
4 Bedrooms
3 Baths
10 Guests
2500 ft²
- Hot Tub
- Spa
- Fireplace/Heating
- Ocean View
US $748/Night
7 Nights - US $5,238
Ski Chalet
10.0(3 Reviews)
4 Bedrooms
2 Baths
11 Guests
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $496/Night
7 Nights - US $3,470
