Chilmark Short Term Stay
3000 ft²
10 Guests
5 Bedrooms
3 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Ocean View
US $1,564/Night
For 7 Nights US $10,947
800 ft²
4 Guests
2 Bedrooms
1 Bathroom
Ocean View
House
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $335/Night
For 7 Nights US $2,346
US $3,473/Night
For 7 Nights US $24,308
3336.81 ft²
8 Guests
1 Bedroom
4 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $914/Night
For 7 Nights US $6,398
3 Guests
1 Bedroom
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Parking
- Air Conditioner
US $1,403/Night
For 7 Nights US $9,821
12 Guests
5 Bedrooms
5 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Ocean View
US $2,518/Night
For 7 Nights US $17,628
1679.17 ft²
8 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $1,895/Night
For 7 Nights US $13,265
8 Guests
4 Bedrooms
5 Bathrooms
Group Friendly
House
US $2,139/Night
For 7 Nights US $14,971
796.53 ft²
4 Guests
1 Bedroom
1 Bathroom
Free Cancellation
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $749/Night
For 7 Nights US $5,243
480 ft²
3 Guests
2 Bedrooms
1 Bathroom
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Ocean View
US $343/Night
For 7 Nights US $2,398
2400.35 ft²
10 Guests
4 Bedrooms
3 Bathrooms
House
- Oceanfront
- Spa
- Fireplace/Heating
US $483/Night
For 7 Nights US $3,381
880 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Ocean View
US $410/Night
For 7 Nights US $2,867
Why Choose Rent By Owner for your Chilmark Short Term Stay?
What makes our Short Term Stay 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 Chilmark
When should you plan your Short Term Stay stay?
To make the most of your getaway, consider visiting during the shoulder seasons when the region offers a peaceful yet vibrant atmosphere, providing ideal conditions for enjoying everything this destination has to offer while securing the best options for your short term stays.
Peak Season Highlights
June to August (Summer)
This is the peak season when the area experiences warm weather and lively outdoor activities, making it ideal for enjoying the scenic beauty of this destination.
Average Temperature Daytime: 75-85°F - Nighttime: 60-65°F
September to October (Fall)
During the fall, the region's landscape transforms with vibrant foliage, attracting visitors seeking a picturesque retreat and outdoor exploration.
Average Temperature Daytime: 65-75°F - Nighttime: 50-55°F
Off-Season Highlights
November to March (Winter)
The winter months bring cooler temperatures and a more tranquil atmosphere, perfect for those looking for a peaceful escape away from crowds.
Average Temperature Daytime: 40-50°F - Nighttime: 30-35°F
April to May (Spring)
Spring offers milder weather and blooming landscapes, providing a quieter opportunity to enjoy the area's natural beauty before the summer rush begins.
Average Temperature Daytime: 55-65°F - Nighttime: 40-45°F
Weekly Weather Forecast for Chilmark
How to Book Your Chilmark Short Term Stay
What's our booking process?
Our platform allows you to browse a curated selection of short term stay. 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 Chilmark
Common Short Term Stay Amenities
What amenities can you expect?
Our Short Term Stay 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 a private outdoor patio or deck to relax and entertain amidst scenic surroundings.
- Take advantage of a well-maintained garden or landscaped yard perfect for outdoor activities.
- Make the most of outdoor dining areas to savor meals al fresco with views of the region's natural beauty.
- Benefit from access to a spacious lawn area ideal for outdoor games or picnics.
- Explore the region’s outdoor lifestyle with amenities like fire pits or outdoor fireplaces for cozy evenings.
- Utilize designated parking spaces or driveways suited for convenient access to outdoor attractions.
- Access outdoor sports equipment such as bicycles, kayaks, or paddleboards to explore the area's scenic waterways and trails.
Top Attractions Around Chilmark
What attractions are nearby?
In this charming area, you can enjoy a variety of outdoor activities and scenic experiences, making your stay here both relaxing and memorable, with opportunities to explore local beaches, nature trails, and cultural sites that showcase the unique character of the region.
Family Activities
- Chilmark Farm and Oyster Farm Tours: Discover the region's rich maritime heritage by exploring local farms that offer family-friendly tours focused on sustainable oyster farming.
- Museum of Island History: Engage your family with educational exhibits highlighting the area's past, providing a meaningful experience for visitors of all ages.
- Beaches in Chilmark: Enjoy relaxing days at some of the most scenic beaches perfect for sandcastle building, swimming, and picnicking with loved ones.
- Nature Walks and Wildlife Watching: Take advantage of scenic trails ideal for family hikes where you can observe native wildlife and enjoy the natural beauty of this destination.
Adult Activities
- Chilmark Vineyard Tours Explore local vineyards to experience the region's renowned wine-making heritage and enjoy tastings in a picturesque setting.
- Squibnocket Beach Relax on this tranquil beach known for its scenic views and opportunities for swimming, surfing, and shoreline walks.
- Art Galleries and Studios Discover the area’s vibrant arts scene through visits to unique galleries and working studios showcasing regional talent.
- Birdwatching Expeditions Engage in guided birdwatching excursions that highlight the region’s diverse avian population and natural beauty.
Other Places to Stay in Chilmark, MA
Dukes County
Fulling Mill Brook Preserve
The Yard
Waskosim's Rock Reservation
Menemsha
Menemsha Beach
Menemsha Blues Charters
Chilmark Chocolates
Lucy Vincent Beach
Squibnocket Pond
Chilmark Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Markets: Take advantage of the area's farmers markets to enjoy fresh, local produce and handcrafted goods that give you a true taste of this destination's community vibe.
- Discover Natural Beauty: Spend time exploring nearby beaches and conservation areas to experience the natural splendor that makes this region a perfect retreat for outdoor enthusiasts.
- Embrace Regional Cuisine: Savor regional flavors at local eateries or pick up ingredients for a memorable meal in your accommodation, immersing yourself in the culinary culture here.
- Plan Off-Peak Visits: Consider visiting during shoulder seasons to enjoy a more relaxed atmosphere, lower prices, and easier access to popular sights within the region.
Transportation Options
- Car Rentals: Renting a car is a flexible way to explore the area at your own pace, with several local providers offering convenient pick-up and drop-off options for your short term stay.
- Taxis and Rideshare Services: Taxis and rideshare options like Uber and Lyft provide easy, on-demand transportation for quick trips around this destination and beyond.
- Bicycling: Biking is a popular and eco-friendly choice here, with dedicated bike paths and scenic routes that allow you to enjoy the region’s natural beauty comfortably.
- Public Transportation: Public transit services connect key points in the area, making it an affordable and practical way to get around during your visit.
Local Customs Options
- Clambakes Participating in traditional clambakes is a cherished custom, offering a genuine taste of local culinary heritage in this coastal region.
- Fisherman’s Traditions Engaging with the area’s fishing community provides insight into longstanding maritime practices that are still celebrated today.
- Harbor Celebrations Local harbor festivals often feature boat parades and communal gatherings, highlighting the area's deep connection to maritime life.
- Preservation of Open Spaces Respectful enjoyment of natural reserves and conservation efforts reflect the community's commitment to maintaining the region’s scenic beauty.
Chilmark Short Term Stay Frequently Asked Questions
1. What are the top Short Term Stays in Chilmark?
There are a lot of options in Chilmark. If you plan on staying in the Chilmark area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Short Term Stays in Chilmark:
- Unwind in Guest House overlooking Menemsha Pond. Dogs ok+ Lv-2 EV charger.
- Mid-Century Modern - All Glass House - Designed By Frank Lloyd Wright Apprentice
- Walk to private beach from beautiful Abels Hill house
- Spectacular Newly Renovated Home in Menemsha
- Vintage 1920s House W/Beach Path & Glorious Sunset Water Views
- Menemsha Pond views & access! Mid-century renovated beach house. Dogs welcome.
- Menemsha - Davis House
- Cool, Mid-Century House - Lucy Vincent Beach and Pool!n
- Secluded house in the woods with deck, streamside firepit, Vincent Beach nearby
- House in Chilmark/Menemsha, Martha's Vineyard w/Private Beach, Sunset View.
2. How many Short Term Stays are available in Chilmark?
Currently, the total number of properties listed by RBO in 2026 is over 2 in the Chilmark area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Short Term Stays in Chilmark.
3. What is the cancellation policy for short term stays in Chilmark, Massachusetts?
Cancellation policies vary depending on the specific listing you choose. It’s recommended to review the cancellation terms directly on the property listing or contact the owner for detailed information.
4. Are there any additional fees I should be aware of when booking a stay in this area?
Additional fees such as cleaning fees, service charges, or taxes may apply. These details are typically outlined in the property listing, and contacting the owner can provide clarification.
5. How do I find the most suitable short term accommodation in Chilmark, Massachusetts?
You can filter options based on your preferences, including amenities, price range, and availability. Reading reviews and contacting hosts directly helps ensure a comfortable stay in this destination.
6. What are the check-in and check-out procedures for stays in the region?
Check-in and check-out times are specified in each listing. Some hosts offer flexible arrangements, so it’s best to confirm these details with the property owner prior to booking.
7. Is there any important information I should know before booking my stay in this part of Massachusetts?
It’s advisable to review the property description carefully and reach out to the owner with any questions. Ensuring clarity on house rules, amenities, and local regulations can enhance your experience here.
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