Best Vacation Homes in Cliff
House
6 Bedrooms
5 Baths
14 Guests
3000 ft²
Private Pool
Fireplace/Heating
Pool
Balcony/Terrace
US $2,592/Night
7 Nights - US $18,146
Bed & Breakfast
10.0(28 Reviews)
1 Bedroom
1 Bath
- Fireplace/Heating
- Balcony/Terrace
Breakfast
Kitchen
US $383/Night
7 Nights - US $2,682
New
House
4 Bedrooms
4 Baths
14 Guests
- Fireplace/Heating
Pet Friendly
Air Conditioner
Internet
US $1,724/Night
7 Nights - US $12,067
House
9.8(6 Reviews)
2 Bedrooms
3 Baths
6 Guests
1603.82 ft²
Oceanfront- Fireplace/Heating
Ocean View- Balcony/Terrace
US $1,930/Night
7 Nights - US $13,510
Apartment
3 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $1,703/Night
7 Nights - US $11,924
New
Apartment
1 Bedroom
1 Bath
4 Guests
- Fireplace/Heating
- Kitchen
- Air Conditioner
- Internet
US $949/Night
7 Nights - US $6,646
Cottage
10.0(295 Reviews)
1 Bedroom
1 Bath
4 Guests
920 ft²
- Oceanfront
Spa- Fireplace/Heating
- Pool
US $1,396/Night
7 Nights - US $9,774
Cliff Luxury Rentals
House
6 Bedrooms
6 Baths
12 Guests
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $8,338/Night
7 Nights - US $58,365
House
2 Bedrooms
3 Baths
4 Guests
4500 ft²
Hot Tub- Fireplace/Heating
- Pool
- Ocean View
US $7,446/Night
7 Nights - US $52,125
House
5 Bedrooms
5 Baths
10 Guests
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $7,021/Night
7 Nights - US $49,146
House
10.0(27 Reviews)
8 Bedrooms
9 Baths
18 Guests
8000 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
US $6,790/Night
7 Nights - US $47,531
House
10.0(8 Reviews)
7 Bedrooms
7 Baths
14 Guests
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
US $6,680/Night
7 Nights - US $46,763
House
10.0(4 Reviews)
5 Bedrooms
7 Baths
12 Guests
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $6,547/Night
7 Nights - US $45,831
US $5,669/Night
7 Nights - US $39,686
House
10.0(50 Reviews)
8 Bedrooms
9 Baths
23 Guests
8300 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $5,473/Night
7 Nights - US $38,313
Cliff Pet Friendly Vacation Rentals
Cottage
10.0(243 Reviews)
2 Bedrooms
2 Baths
6 Guests
1280 ft²
- Oceanfront
- Spa
- Fireplace/Heating
- Pool
US $1,347/Night
7 Nights - US $9,432
Bed & Breakfast
9.5(31 Reviews)
4 Bedrooms
4 Baths
10 Guests
360.59 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $604/Night
7 Nights - US $4,226
House
9.6(5 Reviews)
5 Bedrooms
3 Baths
10 Guests
3500 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Ocean View
US $3,440/Night
7 Nights - US $24,083
Cottage
10.0(241 Reviews)
2 Bedrooms
2 Baths
6 Guests
1725 ft²
- Oceanfront
- Spa
- Fireplace/Heating
- Pool
US $1,634/Night
7 Nights - US $11,435
Bed & Breakfast
9.3(29 Reviews)
12 Bedrooms
5 Baths
14 Guests
254.03 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $175/Night
7 Nights - US $1,225
House
10.0(182 Reviews)
1 Bedroom
1 Bath
4 Guests
- Oceanfront
- Spa
- Fireplace/Heating
- Pool
US $1,247/Night
7 Nights - US $8,731
Cottage
10.0(167 Reviews)
2 Bedrooms
1 Bath
5 Guests
840 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $1,100/Night
7 Nights - US $7,702
Cottage
10.0(128 Reviews)
1 Bedroom
1 Bath
2 Guests
1025 ft²
- Oceanfront
- Spa
- Fireplace/Heating
- Pool
US $1,247/Night
7 Nights - US $8,731
Cliff Large Vacation Homes
House
10.0(88 Reviews)
5 Bedrooms
2 Baths
11 Guests
1800 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $1,553/Night
7 Nights - US $10,868
Bed & Breakfast
9.7(53 Reviews)
13 Bedrooms
13 Baths
26 Guests
231.84 ft²
- Fireplace/Heating
- Balcony/Terrace
View- Breakfast
US $879/Night
7 Nights - US $6,153
House
10.0(77 Reviews)
5 Bedrooms
5 Baths
14 Guests
4500 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
US $2,368/Night
7 Nights - US $16,576
Cabin
9.5(22 Reviews)
13 Bedrooms
13 Baths
28 Guests
245.91 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $419/Night
7 Nights - US $2,933
House
10.0(76 Reviews)
4 Bedrooms
4 Baths
12 Guests
3326 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
US $1,452/Night
7 Nights - US $10,165
Apartment
10.0(76 Reviews)
3 Bedrooms
1 Bath
10 Guests
1200 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- View
US $1,229/Night
7 Nights - US $8,601
House
10.0(65 Reviews)
5 Bedrooms
8 Baths
14 Guests
5100 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
US $2,457/Night
7 Nights - US $17,199
House
10.0(62 Reviews)
5 Bedrooms
5 Baths
10 Guests
4000 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $2,312/Night
7 Nights - US $16,185
Why Choose Rent By Owner for your Cliff Vacation Rental Homes?
What makes our 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.
Popular Areas for Cliff Vacation Rentals
Where are the best neighborhoods to stay in Cliff?
When planning your trip to Nantucket, Massachusetts, exploring the neighborhoods within Cliff can enhance your stay by offering a peaceful and scenic setting. This charming area provides an ideal backdrop for relaxing in comfortable vacation rentals while enjoying the natural beauty of the island. Whether you prefer a quiet retreat or a central location close to local amenities, finding the perfect neighborhood in Cliff ensures a memorable and enjoyable visit to Nantucket. With a range of reliable accommodations, you'll experience a seamless booking process that makes your getaway both convenient and dependable.
Nantucket Town
This central neighborhood offers convenient access to the heart of the island, making it an ideal choice for those seeking a lively atmosphere and proximity to local shops and eateries. Staying here provides a vibrant base to explore the area's historic charm and scenic beauty.
View 460+ Rentals in Nantucket TownBrant Point
Located near the harbor, this neighborhood is perfect for visitors wanting stunning waterfront views and easy access to ferry services. It’s an excellent spot for those looking to enjoy the tranquil seaside ambiance while remaining close to the region's main attractions.
View 28+ Rentals in Brant PointDionis
Set amidst serene natural surroundings, Dionis offers a peaceful retreat away from busier areas, ideal for travelers who value privacy and scenic beaches. Here, you can immerse yourself in the quiet beauty of the region while still being within reach of local amenities.
View 780+ Rentals in DionisBest Times to Visit Cliff
When should you plan your Vacation Rentals stay?
Choosing the right time to visit this charming destination ensures you experience its serene beaches and picturesque surroundings at their best, making your stay in the area truly memorable.
Peak Season Highlights
Summer (June to August)
During the summer months, the area experiences its peak season, making it ideal for enjoying warm weather and lively coastal activities.
Average Temperature Daytime: 75°F to 80°F - Nighttime: 60°F to 65°F
Fall (September to October)
Early fall offers pleasant temperatures and fewer crowds, perfect for exploring and relaxing in this popular destination before the winter chill sets in.
Average Temperature Daytime: 68°F to 72°F - Nighttime: 55°F to 58°F
Off-Season Highlights
Winter (November to February)
In winter, you can enjoy a quieter atmosphere with fewer tourists, ideal for those seeking tranquility and scenic winter views.
Average Temperature Daytime: 45°F to 50°F - Nighttime: 35°F to 40°F
Spring (March to May)
Springtime brings milder weather and blooming landscapes, making it a charming time to visit and secure more affordable vacation rentals.
Average Temperature Daytime: 55°F to 65°F - Nighttime: 45°F to 50°F
Weekly Weather Forecast for Cliff
How to Book Your Cliff Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of 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 Cliff
Common Vacation Rentals Amenities
What amenities can you expect?
Our 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 outdoor dining spaces perfect for hosting meals amidst the scenic surroundings.
- Take advantage of a private or shared pool to relax and cool off during your stay.
- Experience the convenience of well-maintained outdoor patios or decks for lounging and entertaining.
- Make the most of lush, landscaped yards ideal for outdoor activities or picnics.
- Benefit from direct access to nearby beaches or waterfront areas for water-based adventures.
- Utilize outdoor shower facilities to rinse off after beach days or outdoor activities.
- Secure parking options to conveniently explore the region’s popular outdoor spots and attractions.
Top Attractions Around Cliff
What attractions are nearby?
Within this charming region, you can enjoy leisurely strolls along scenic beaches, explore quaint local shops, or take in the natural beauty of nearby coastal trails, all conveniently accessible from your vacation rental.
Family Activities
- Cliff Walk Exploration: Stroll along the scenic coastal trail offering breathtaking views and fun opportunities for family photos in this charming area.
- Nantucket Whaling Museum: Discover fascinating exhibits about the region's maritime history, perfect for engaging young minds and learning together as a family.
- Children’s Beach at Jetties Beach: Enjoy a relaxing day building sandcastles and swimming at this popular family-friendly spot with calm waters near the area.
- Summer Events and Festivals: Participate in local seasonal celebrations and outdoor activities that foster family bonding and create lasting memories here.
Adult Activities
- Beachcombing and Coastal Walks: Explore the rugged shoreline along here, where you can enjoy peaceful walks and discover hidden seashells and marine life.
- Whale Watching Tours: Embark on a guided excursion to witness the majestic marine mammals in their natural habitat, a highlight of the region's maritime charm.
- Sailing and Boating Adventures: Rent a boat or join a sailing tour to experience the scenic waters surrounding this destination from a unique perspective.
- Historic Site Visits: Discover the area's rich maritime history by exploring local landmarks and preserved structures that reflect its coastal heritage.
Other Places to Stay in Cliff, MA
Jethro Coffin House
Founder's Cemetery
Cliff Travel Tips
How Can You Make the Most of Your Stay?
- Explore the local beaches: Take advantage of the region's scenic shoreline by visiting nearby beaches to relax and enjoy the coastal atmosphere.
- Visit local eateries: Savor fresh seafood and regional specialties at dining spots that highlight the area's culinary charm.
- Discover charming neighborhoods: Stroll through the quaint streets and explore the unique architecture that characterizes this destination's community vibe.
- Plan outdoor activities: Engage in outdoor pursuits like biking or walking along scenic routes to fully immerse yourself in the area's natural beauty.
Transportation Options
- North Wharf Ferry Terminal: You can easily access Nantucket from here via ferry, providing a scenic and convenient way to arrive close to your vacation rental in the area.
- Nantucket Memorial Airport: This regional airport offers scheduled flights that make traveling to this destination quick and straightforward for visitors coming from various locations.
- Private Boat Charters: For a personalized experience, consider booking a private boat charter to explore nearby waters and arrive directly to your rental by sea.
- Rental Cars and Taxis: Local rental agencies and taxi services offer flexible transportation options around the region, ensuring you can easily reach your vacation rental and explore here at your own pace.
Local Customs Options
- Harbor Greeting Tradition: Locals here often greet visitors and neighbors with friendly waves and warm welcomes, reflecting the community's maritime heritage.
- Cliff Dwelling Etiquette: Respect for private property and historic cliff-side homes is highly valued, so be mindful when exploring the area’s scenic neighborhoods.
- Seaside Celebrations: Community events frequently celebrate the region's coastal culture, providing an authentic experience of local customs and traditions.
- Fresh Seafood Appreciation: Enjoying locally caught seafood at neighborhood gatherings or restaurants is a cherished custom that highlights the area's culinary roots.
Frequently Asked Questions About Cliff?
1. What are the top vacation rentals in Cliff?
There are a lot of options in Cliff. If you plan on staying in the Cliff area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Cliff:
- Luxurious Harbor View “Eliza” Cottage! Next To White Elephant!
- Luxurious Harbor View "Millie" Cottage! Walk & bike to everything!
- Luxurious Harbor View “Cynthia” cottage. Walk & bike to everything!
- LUXURIOUS New Cottage! 5-min. walk to Main St. And Harbor Beaches
- Renovated Cottage off Main Street- Great Location
- Charming, Convenient Mid-Island Nantucket Cottage on Surfside Beach Bike Path
- OCTOBER DISCOUNTS! JUST ASK.BEAUTIFUL COTTAGE on ORANGE ST, WALK TO MAIN STREET!
- Walk to Town from Beautiful Cottage w/Guest House & A/C 3bed/3bath!
- Charming cottage, close to lower Main Street.
- Luxurious Harbor View "Lizzie" Cottage! Walk & bike to everything!
2. How many vacation rentals have private pools in Cliff?
There are 129 vacation rentals with private pools near Cliff. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Cliff are best for families?
If you are looking for a family-friendly vacation home in Cliff, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Cliff:
4. How many Rentbyowner vacation rentals are available in Cliff?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 1065 in the Cliff 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 Cliff.
5. What is the cancellation policy for a vacation rental in Cliff?
Cancellation policies vary depending on the property owner. To ensure you understand the specific terms, please review the listing details or contact the owner directly before booking.
6. Are there any additional fees or charges I should be aware of when booking here?
Additional fees such as cleaning, service charges, or security deposits are specified in each listing. It’s best to read the full details on the property page or reach out to the owner for clarification.
7. How do I confirm my reservation and what payment methods are accepted?
Reservations are confirmed through the booking platform after your payment is processed. Accepted payment methods typically include credit cards and digital payments; check the listing for specific options.
8. Is it possible to request special amenities or accommodations for my stay?
Many hosts are open to accommodating special requests, but it’s advisable to contact the owner directly prior to booking to discuss your needs and ensure they can be met.
9. What should I know about accessing the property upon arrival?
Property access details, including check-in instructions, are provided after booking. Be sure to review these instructions carefully or contact the host if you need further assistance.
Cliff Top Rated Vacation Rentals
House
10.0(71 Reviews)
4 Bedrooms
4 Baths
8 Guests
- Oceanfront
- Hot Tub
- Spa
- Fireplace/Heating
US $3,435/Night
7 Nights - US $24,043
House
10.0(63 Reviews)
4 Bedrooms
3 Baths
8 Guests
2200 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
US $1,744/Night
7 Nights - US $12,211
House
10.0(57 Reviews)
4 Bedrooms
5 Baths
12 Guests
4000 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Ocean View
US $1,992/Night
7 Nights - US $13,944
House
10.0(50 Reviews)
4 Bedrooms
3 Baths
8 Guests
2000 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
US $1,323/Night
7 Nights - US $9,258
House
10.0(44 Reviews)
7 Bedrooms
6 Baths
16 Guests
3500 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $3,435/Night
7 Nights - US $24,046
House
10.0(41 Reviews)
6 Bedrooms
4 Baths
13 Guests
4688 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Ocean View
US $3,223/Night
7 Nights - US $22,558
House
10.0(34 Reviews)
7 Bedrooms
6 Baths
16 Guests
5500 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $2,681/Night
7 Nights - US $18,766
