Best Vacation Homes in Ashford
House
10.0(74 Reviews)
2 Bedrooms
1 Bath
6 Guests
900 ft²
Fireplace/Heating
Ocean View
Balcony/Terrace
View
R6,466/Night
7 Nights - R45,261
House
10.0(3 Reviews)
3 Bedrooms
2 Baths
8 Guests
1506.95 ft²
Spa
Skiing- Fireplace/Heating
- View
R4,255/Night
7 Nights - R29,783
House
8.8(121 Reviews)
1 Bedroom
1 Bath
- Balcony/Terrace
Kitchen
Parking
Air Conditioner
R4,249/Night
7 Nights - R29,750
Cottage
10.0(46 Reviews)
3 Bedrooms
1 Bath
8 Guests
1200 ft²
Oceanfront- Fireplace/Heating
- Ocean View
- Balcony/Terrace
R5,388/Night
7 Nights - R37,721
House
10.0(2 Reviews)
2 Bedrooms
2 Baths
4 Guests
1399.31 ft²
- Fireplace/Heating
Pool
Pet Friendly- Parking
R6,135/Night
7 Nights - R42,946
Cottage
10.0(31 Reviews)
2 Bedrooms
2 Baths
4 Guests
1400 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
R5,479/Night
7 Nights - R38,349
Cottage
10.0(24 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
R6,067/Night
7 Nights - R42,467
House
10.0(21 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
R4,017/Night
7 Nights - R28,129
Ashford Luxury Rentals
House
10.0(6 Reviews)
5 Bedrooms
5 Baths
15 Guests
5746 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
R35,087/Night
7 Nights - R245,606
House
9.8(56 Reviews)
6 Bedrooms
4 Baths
25 Guests
5500 ft²
Private Pool- Oceanfront
Hot Tub- Fireplace/Heating
R30,142/Night
7 Nights - R210,994
New
House
5 Bedrooms
2 Baths
10 Guests
4822.23 ft²
- Fireplace/Heating
- View
Internet
Sports/Activities
R20,354/Night
7 Nights - R142,482
House
10.0(10 Reviews)
5 Bedrooms
3 Baths
10 Guests
3600 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Ocean View
R18,685/Night
7 Nights - R130,790
House
3 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Air Conditioner
- Internet
Child Friendly
R17,931/Night
7 Nights - R125,515
House
5 Bedrooms
5 Baths
10 Guests
4822 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
R17,131/Night
7 Nights - R119,909
House
10.0(1 Review)
4 Bedrooms
2 Baths
10 Guests
- Child Friendly
Security/Safety
R15,214/Night
7 Nights - R106,498
House
10.0(2 Reviews)
3 Bedrooms
2 Baths
8 Guests
1300 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
R14,168/Night
7 Nights - R99,172
Ashford Pet Friendly Vacation Rentals
Ski Chalet
10.0(15 Reviews)
2 Bedrooms
2 Baths
4 Guests
2000 ft²
- Spa
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
R6,787/Night
7 Nights - R47,511
House
1 Bedroom
3 Baths
7 Guests
2002.09 ft²
- Fireplace/Heating
- View
- Pet Friendly
- Air Conditioner
R6,386/Night
7 Nights - R44,699
Cottage
1 Bedroom
1 Bath
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
R7,043/Night
7 Nights - R49,297
House
10.0(3 Reviews)
2 Bedrooms
1 Bath
7 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
R3,645/Night
7 Nights - R25,516
Hotel
9.1(359 Reviews)
1 Bath
3805.81 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
R5,091/Night
7 Nights - R35,637
House
10.0(1 Review)
2 Bedrooms
2 Baths
4 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
R4,365/Night
7 Nights - R30,560
House
9.8(29 Reviews)
2 Bedrooms
1 Bath
5 Guests
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
R5,773/Night
7 Nights - R40,416
Cottage
9.4(26 Reviews)
2 Bedrooms
1 Bath
5 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
R3,848/Night
7 Nights - R26,939
Ashford Large Vacation Homes
Apartment
10.0(2 Reviews)
3 Bedrooms
2 Baths
16 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
R6,194/Night
7 Nights - R43,360
Bed & Breakfast
9.5(70 Reviews)
3 Bedrooms
3 Baths
12 Guests
340.86 ft²
- Fireplace/Heating
- Balcony/Terrace
- View
- Parking
R3,390/Night
7 Nights - R23,730
House
10.0(6 Reviews)
5 Bedrooms
3 Baths
7 Guests
- Hot Tub
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
R10,877/Night
7 Nights - R76,136
House
7 Bedrooms
7 Baths
14 Guests
5500.36 ft²
- Parking
- Internet
- Child Friendly
Wheelchair Accessible
R9,658/Night
7 Nights - R67,603
House
10.0(2 Reviews)
6 Bedrooms
6 Baths
12 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
R7,942/Night
7 Nights - R55,597
House
9.6(35 Reviews)
3 Bedrooms
2 Baths
12 Guests
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
R7,536/Night
7 Nights - R52,753
R6,307/Night
7 Nights - R44,154
House
9.8(8 Reviews)
6 Bedrooms
3 Baths
18 Guests
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
R16,690/Night
7 Nights - R116,833
Why Choose Rent By Owner for your Ashford 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.
Best Times to Visit Ashford
When should you plan your Vacation Rentals stay?
Choosing the right time to visit here can enhance your experience, as seasonal variations in this destination offer unique opportunities for enjoyment throughout the year.
Peak Season Highlights
Summer (June to August)
During the summer months, you can enjoy warm weather ideal for outdoor activities and exploring the scenic surroundings of this destination.
Average Temperature Daytime: 75°F to 85°F - Nighttime: 60°F to 65°F
Fall (September to November)
In early fall, the region offers vibrant foliage viewing, making it a popular time for travelers seeking picturesque views and mild temperatures.
Average Temperature Daytime: 65°F to 75°F - Nighttime: 50°F to 55°F
Off-Season Highlights
Winter (December to February)
The winter season brings cooler weather, perfect if you prefer a quieter getaway with opportunities for cozy indoor relaxation.
Average Temperature Daytime: 30°F to 40°F - Nighttime: 20°F to 25°F
Spring (March to May)
In spring, the area begins to bloom, offering a peaceful atmosphere and fewer visitors for a more private escape.
Average Temperature Daytime: 50°F to 60°F - Nighttime: 35°F to 45°F
Weekly Weather Forecast for Ashford
How to Book Your Ashford 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 Ashford
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 with a fully equipped patio or BBQ area.
- Relax by a private or shared swimming pool nestled in the scenic surroundings.
- Take advantage of lush garden spaces perfect for picnics or outdoor gatherings.
- Experience the tranquility of a furnished porch or deck with scenic views of the region.
- Explore the natural landscape through nearby walking trails or hiking paths.
- Benefit from parking facilities designed to accommodate your outdoor adventure needs.
- Make use of outdoor recreational amenities such as tennis courts or playgrounds available on-site.
Top Attractions Around Ashford
What attractions are nearby?
In this charming destination, you can enjoy a variety of outdoor activities such as hiking, fishing, and exploring scenic parks that highlight the natural beauty of the region.
Family Activities
- Hike the Mashamoquet Brook State Park Trails: Explore scenic walking trails that provide a fun and educational outdoor experience for your family here in the area.
- Visit the Sport Shipping Museum: Discover local history through engaging exhibits, perfect for sparking curiosity and learning during your stay.
- Enjoy a Day at Candlewood Lake: Spend quality time by the water with boating, fishing, or simply relaxing along the shoreline, ideal for family outings in this region.
- Explore the Ashford Town Historical Society: Immerse your family in the area's rich heritage through unique exhibits and historical programs tailored for visitors of all ages.
Adult Activities
- Hiking at Bigelow Hollow State Park: Explore scenic trails and enjoy panoramic views within this expansive state park, a perfect outdoor activity for nature enthusiasts staying nearby.
- Visiting the Connecticut Explored Museum: Dive into regional history and local culture through engaging exhibits that highlight the area's heritage and natural environment.
- Golf at Goodwin Park Golf Course: Spend a relaxing day on the lush fairways of this charming golf course, offering an enjoyable experience for players of all skill levels.
- Fishing in the area’s lakes and streams: Cast your line in the region’s serene waters, providing an ideal setting for anglers seeking tranquility and freshwater fishing opportunities.
Other Places to Stay in Ashford, CT
Tinkerville Brook Reserve
Ashford Travel Tips
How Can You Make the Most of Your Stay?
- Explore local outdoor activities: Take advantage of the scenic trails and parks nearby to enjoy the natural beauty that makes this destination unique.
- Plan your visit around seasonal events: Check out the area’s seasonal festivals or markets to experience authentic local culture during your stay.
- Select the right vacation rental: Choose a well-reviewed property that offers comfort and convenience, ensuring a relaxing and enjoyable visit here.
- Discover nearby dining options: Sample the regional cuisine at local eateries to get a true taste of the region’s flavors during your trip.
Transportation Options
- Connecticut Transit Bus Services: Local bus routes in the area offer an affordable and convenient way to explore here without the need for a car.
- Shuttle Services: Airport shuttles provide seamless transportation from nearby airports directly to your vacation rental, making arrivals and departures effortless.
- Car Rentals: Renting a vehicle is a flexible option for exploring the region at your own pace, with several providers available nearby.
- Taxi and Ride-Sharing: Taxis and ride-sharing services are readily accessible for quick trips within this destination and surrounding areas.
Local Customs Options
- Local Farmers' Markets: Visiting the area’s farmers’ markets offers a glimpse into the region’s fresh produce and community spirit, making it a great way to experience local culture during your stay.
- Traditional Holiday Celebrations: Participating in seasonal festivities here allows you to enjoy authentic regional customs and connect with the friendly locals in this destination.
- Regional Dining Etiquette: When dining in local establishments, you'll find that casual yet courteous interactions reflect the welcoming nature of the region's hospitality.
- Community Events and Fairs: Attending neighborhood events provides an opportunity to immerse yourself in the area's traditions and meet residents who are proud of their heritage.
Frequently Asked Questions About Ashford?
1. What are the top vacation rentals in Ashford?
There are a lot of options in Ashford. If you plan on staying in the Ashford area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Ashford:
- Weekend Weddings on our Farm.
- Little Dipper Retreat Lakefront Cottage, Sunsets & Kayaks!
- The Bungalow at Eagleville Lake nUnder 3 miles to UCONN!
- Chic Lakehouse with a gorgeous view
- Magical Waterfront Cottage! Pet friendly!
- Updated Lakefront House *outdoor tv and water toys- 10 min from UConn
- The Maybrook: Lake & Sauna
- Lakefront Connecticut Retreat Near UConn
- Lake Getaway at Coventry Lake! close to Uconn
- Stunning Lakefront Escape! Book Your Dream Getaway!
2. Which vacation homes in Ashford are best for families?
If you are looking for a family-friendly vacation home in Ashford, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Ashford:
3. How many Rentbyowner vacation rentals are available in Ashford?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 152 in the Ashford 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 Ashford.
4. What is the cancellation policy for vacation rentals in Ashford, Connecticut?
Cancellation policies vary by property, so it’s essential to review the specific listing details. You can find this information in the rental’s terms or contact the owner directly for clarification.
5. How do I secure my reservation at a vacation rental in this area?
Reservations are typically secured through the booking platform with a deposit or full payment, depending on the property’s policies. Be sure to read the listing carefully and communicate with the owner if needed before finalizing your booking.
6. Are there any additional fees when booking a vacation rental in this region?
Additional fees such as cleaning fees, service charges, or local taxes may apply. These will be detailed in the listing, so review all costs before confirming your reservation.
7. What amenities can I expect in a vacation rental here?
Amenities vary by property but often include essentials like Wi-Fi, parking, and kitchen facilities. Check the specific listing to see what amenities are offered to ensure they meet your needs.
8. Is it possible to modify or cancel my booking if plans change?
Modification and cancellation options depend on the property's policies. Contact the property owner directly or review the terms outlined in the listing to understand your options if your plans change.
Ashford Top Rated Vacation Rentals
Other
10.0(92 Reviews)
3 Bedrooms
1 Bath
8 Guests
7000 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
Breakfast
R6,504/Night
7 Nights - R45,526
R2,214/Night
7 Nights - R15,495
Hotel
7.1(152 Reviews)
1 Bath
293.32 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
R2,713/Night
7 Nights - R18,984
R1,277/Night
7 Nights - R8,946
House
10.0(41 Reviews)
3 Bedrooms
2 Baths
6 Guests
1800 ft²
- Hot Tub
- Spa
- Fireplace/Heating
- Pool
R4,945/Night
7 Nights - R34,612
Cabin
10.0(1 Review)
3 Bedrooms
1 Bath
8 Guests
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
R5,814/Night
7 Nights - R40,697
Cabin
10.0(1 Review)
2 Bedrooms
1 Bath
2 Guests
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
R3,456/Night
7 Nights - R24,193
House
6 Bedrooms
4 Baths
18 Guests
5200 ft²
- Private Pool
- Pool
- Air Conditioner
- Internet
R21,035/Night
7 Nights - R147,245
