Stamford holiday homes

We found 371 holiday rentals — enter your dates for availability
Discover a selection of holiday rentals in Stamford that are perfect for your trip. Whether you're travelling with your children or with friends, holiday rentals have the amenities that you need and want for your stay, which might include a hot tub and a washer and dryer. No matter what you're looking for, you'll be sure to find a property to rent for everyone's needs, including accessible or non-smoking choices.

Holiday rentals with weekly discounts – Stamford

Showing deals for:18 Dec - 25 Dec

Exterior
Terrace/patio
Two story living room with 70" smarttv, premium directtv and bluetooth turntable
Indoor hot tub
Exceptional
(10 reviews)

HotTub&GameRm&Traeger Smoker-15 min 2 Mt Snow, Across from Golf, 5 min to Lake

Wilmington

16% off
NZ$10,304
for 7 nights, 1 chalet
NZ$1,472 per night
includes taxes & fees
HotTub&GameRm&Traeger Smoker-15 min 2 Mt Snow, Across from Golf, 5 min to Lake
Summer view from the lake
A beautiful brook that runs through our lot
Enjoy chess, checkers or backgammon
Silestone counter top and Hickory cabinets
Exceptional
(101 reviews)

New Lakefront Log Home

Wilmington

12% off
NZ$7,282
for 7 nights, 1 chalet
NZ$1,040 per night
includes taxes & fees
New Lakefront Log Home
Early morning summer view
View out front door
View from Kitchen sink
Dining area, 10 Chairs are now black, Need a new picture!
Exceptional
(243 reviews)

Amazing lake views & access,HotTub & sauna, quality game Rm. 230-10 star Reviews

Wilmington

8% off
NZ$9,143
for 7 nights, 1 home
NZ$1,306 per night
includes taxes & fees
Amazing lake views & access,HotTub & sauna, quality game Rm. 230-10 star Reviews
Build a cozy fire in our wood fireplace, watch the game or play pool!
Beautiful period woodwork and Victorian details
Walk to Spring Street and brand new Williams Bookstore
Gourmet kitchen has everything you need to prepare delicious meals
Exceptional
(157 reviews)

Huge Luxe Williamstown Updated Victorian, All Ensuite Baths, Walk to Spring St!

Williamstown

7% off
NZ$10,304
for 7 nights, 1 home
NZ$1,472 per night
includes taxes & fees
Huge Luxe Williamstown Updated Victorian, All Ensuite Baths, Walk to Spring St!
Private kitchen
Terrace/patio
Room
Dining
Exceptional
(20 reviews)

Family-friendly, private three bedroom cottage in the beautiful Berkshires

Williamstown

12% off
NZ$5,103
for 7 nights, 1 cottage
NZ$729 per night
includes taxes & fees
Family-friendly, private three bedroom cottage in the beautiful Berkshires
Private kitchen
Interior
Dining
Exterior
Exceptional
(6 reviews)

Grateful Getaway - 5BR, 3.5B Home Sleeps 10 - Close to Mount Snow!

Wilmington

7% off
NZ$13,379
for 7 nights, 1 home
NZ$1,911 per night
includes taxes & fees
Grateful Getaway - 5BR, 3.5B Home Sleeps 10 - Close to Mount Snow!
Interior
Outdoor dining
Property grounds
Dining
Exceptional
(39 reviews)

Large, family-friendly farmhouse located in the beautiful Berkshires

Williamstown

20% off
NZ$6,713
for 7 nights, 1 home
NZ$959 per night
includes taxes & fees
Large, family-friendly farmhouse located in the beautiful Berkshires
Interior
Indoor spa tub
Dining
Games room
Exceptional
(53 reviews)

SKIING, PARTY SAFELY IN THE SNOW! NO NEED TO DRINK & DRIVE.

Wilmington

8% off
NZ$14,299
for 7 nights, 1 home
NZ$2,043 per night
includes taxes & fees
SKIING, PARTY SAFELY IN THE SNOW! NO NEED TO DRINK & DRIVE.
Kitchen and dining area.
View from deck.
Room
Living area
Exceptional
(25 reviews)

Spacious/Elegant 3 level house on Spruce Lake- swim or fish, short drive to Mt.

Wilmington

18% off
NZ$9,185
for 7 nights, 1 home
NZ$1,312 per night
includes taxes & fees
Spacious/Elegant 3 level house on Spruce Lake- swim or fish, short drive to Mt.
Property grounds
Outdoor dining
Exterior
Living area
Exceptional
(31 reviews)

Secluded large country home for big groups with giant open yard for outdoor fun.

Whitingham

20% off
NZ$4,329
for 7 nights, 1 home
NZ$618 per night
includes taxes & fees
Secluded large country home for big groups with giant open yard for outdoor fun.
Room
Private kitchen
Private kitchen
Living area
Exceptional
(19 reviews)

Cozy Condo Near MASS MoCA

North Adams

12% off
NZ$4,647
for 7 nights, 1 home
NZ$664 per night
includes taxes & fees
Cozy Condo Near MASS MoCA
Living room with fireplace and 55" smart tv
Open floorplan
Outdoor firepit with plenty of seating
Fully stocked kitchen with gas range
Exceptional
(11 reviews)

Large rustic home with gameroom. Near lakes, skiing, walk to downtown.

Wilmington

12% off
NZ$11,984
for 7 nights, 1 home
NZ$1,712 per night
includes taxes & fees
Large rustic home with gameroom. Near lakes, skiing, walk to downtown.
Room
Owner and guest parking. Private guest access is located through the porch door.
Hallway view from the bathroom looking toward the kitchen area.
Exterior detail
Exceptional
(34 reviews)

Getaway Near Mass MoCA, Great Hiking, Scenic Views

Stamford

8% off
NZ$1,688
for 7 nights, 1 apartment
NZ$241 per night
includes taxes & fees
Getaway Near Mass MoCA, Great Hiking, Scenic Views
Room
Living area
Dining
Outdoor dining
Exceptional
(5 reviews)

Charming Home with Lake and Mountain View

Whitingham

8% off
NZ$11,014
for 7 nights, 1 cabin
NZ$1,573 per night
includes taxes & fees
Charming Home with Lake and Mountain View
Dining room
MassMoCA in nearby North Adams, Mass
Living room
Exterior
Exceptional
(13 reviews)

Family Home in the mountains. Get out and explore!

Monroe

16% off
NZ$2,136
for 7 nights, 1 home
NZ$305 per night
includes taxes & fees
Family Home in the mountains. Get out and explore!
View from our kitchen window in the summer
Fully stocked renovated kitchen
Living room with woodstove, TV, and french doors looking out to our land
Dining room (view from the kitchen)
Exceptional
(18 reviews)

Spruce Hill Farm - 1850 Farmhouse on 50 Acres - Minutes to Mt Snow!!

Wilmington

8% off
NZ$11,288
for 7 nights, 1 home
NZ$1,613 per night
includes taxes & fees
Spruce Hill Farm - 1850 Farmhouse on 50 Acres - Minutes to Mt Snow!!
Interior
Interior
Living area
Exterior
Exceptional
(97 reviews)

The Green Mountain Roost, Very Private & Quiet Country House, Dogs Welcome

Whitingham

11% off
NZ$2,926
for 7 nights, 1 home
NZ$418 per night
includes taxes & fees
The Green Mountain Roost, Very Private & Quiet Country House, Dogs Welcome
Living area
Rear Entry Staircase & Sun Room
Interior
Bow Window in Master Bedroom Overlooking Main Street
Exceptional
(11 reviews)

Luxury Living High Above the Center of Town.

Bennington

8% off
NZ$3,734
for 7 nights, 1 apartment
NZ$533 per night
includes taxes & fees
Luxury Living High Above the Center of Town.
Dining
Exterior
Pool
Interior
Very good
(6 reviews)

Crafts Inn, Hotel Suite with pool and hot tub.

Wilmington

8% off
NZ$3,374
for 7 nights, 1 room
NZ$482 per night
includes taxes & fees
Crafts Inn, Hotel Suite with pool and hot tub.
Interior
Living area
Interior
Living area
Very good
(5 reviews)

Walk to campus; open concept kitchen/living;nature trail at end of this quiet st

Williamstown

14% off
NZ$3,545
for 7 nights, 1 home
NZ$506 per night
includes taxes & fees
Walk to campus; open concept kitchen/living;nature trail at end of this quiet st
Front covered porch for people watching and catching summer breezes.
Exterior
Interior
Room
Exceptional
(7 reviews)

Downtown Victorian House

Bennington

12% off
NZ$2,918
for 7 nights, 1 apartment
NZ$417 per night
includes taxes & fees
Downtown Victorian House

  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Choose a holiday rental for your Stamford getaway

Learn about the unique charm of Stamford with a stay in a holiday home rental. This city has something for everyone. If you're looking for accommodation options with space to entertain friends and family, HomeAway has plenty of options to choose from. Many rental homes offer full kitchens and laundry facilities, perfect for big groups.

Activities and attractions in Stamford

Are you looking for top things to see and do in the area? Venture out of your cosy holiday rental and check out everything that makes Stamford a fun spot to go on holiday. These are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Prospect Mountain Cross-Country Ski Center (8.2 mi / 13.2 km)
  • Waubeeka Golf Links (11.1 mi / 17.9 km)
  • The Hermitage Golf Club (13.4 mi / 21.6 km)
  • Berkshire East Ski Resort (13.8 mi / 22.2 km)
  • The Hermitage Club (14.2 mi / 22.9 km)
  • Mount Snow (16 mi / 25.7 km)

Exploring the natural landscape of Stamford

Whether you're looking for fun outdoor activities or just want to spend some time taking in the scenery, Stamford is a great place to get outside. Here are some of the area’s most stunning natural features, all within 30 miles (48.2 km) of the city centre:

  • Mount Greylock (9.6 mi / 15.5 km)
  • Mount Greylock State Reservation (9.8 mi / 15.8 km)
  • Harriman Reservoir (10 mi / 16.1 km)
  • Jacksonville Pond (13 mi / 20.9 km)
  • Lake Raponda (15.1 mi / 24.3 km)
  • Hogback Mountain Conservation Area (15.6 mi / 25.2 km)

Transport options to and around Stamford

The nearest airport is in Pittsfield, MA (PSF-Pittsfield Municipal), located 25.5 mi (41.1 km) from the city centre.

Frequently asked questions

What is the best area to stay in Stamford when booking a holiday rental?
When considering a holiday rental in Stamford, Vermont, the area around the picturesque village centre is often regarded as the most appealing. This charming location offers a peaceful rural atmosphere, superb for those looking to escape the hustle and bustle of city life. You'll find a variety of properties available, suiting different preferences, from quaint cottages to more spacious homes.Stamford is well-known for its stunning natural surroundings, making it an ideal choice for outdoor enthusiasts. The nearby Green Mountain National Forest provides ample opportunities for hiking and enjoying the breathtaking scenery. Additionally, the area is close to the lovely Harriman Reservoir, which is superb for fishing, boating, and picnicking.Exploring the local attractions, visitors can appreciate the rich history and beauty of the region. The serene landscapes and friendly community create a welcoming environment, making your stay not just comfortable but also memorable.
Where are the best Stamford ski resort rentals?
For the best ski resort rentals in Stamford, Vermont, visitors should consider accommodations near the Stratton Mountain Resort, which is just a short drive away. The area around Stratton offers a variety of rental options, including charming chalets and spacious condos, many of which feature amenities such as ski-in/ski-out access, fireplaces, and hot tubs, great for relaxing after a day on the slopes.In Stamford itself, travellers can find cosy cabins and lodges that provide a more secluded experience, often surrounded by the natural beauty of the Green Mountains. These properties typically come equipped with kitchen facilities for self-catering, comfortable living areas, and outdoor spaces for enjoying the serene landscape.Additionally, the nearby town of Wilmington offers more rental possibilities, with easy access to the mountain as well as local shops and restaurants. Rentals in this area are often family-friendly, featuring multiple bedrooms and communal spaces, ideal for groups looking to enjoy both skiing and the quaint charm of Vermont's small towns.
What is the most popular type of holiday rental accomodation in Stamford?
In Stamford, holiday houses are the most popular type of holiday rental, with several available throughout the area. These houses typically offer spacious living arrangements, including multiple bedrooms, fully equipped kitchens, and outdoor spaces, making them ideal for families or groups looking to enjoy the scenic beauty of Vermont. Additionally, there are several apartments that provide a more compact, yet comfortable option for travellers. These apartments often feature modern amenities, such as kitchen facilities and cosy living areas, superb for unwinding after a day of exploring the local surroundings.
Are there any family house rentals in Stamford?
In Stamford, Vermont, there are several family-friendly house rentals available, making it an excellent choice for those looking to enjoy a getaway with loved ones. The area features spacious homes that often come equipped with multiple bedrooms, allowing families to comfortably settle in. Many properties include full kitchens, enabling visitors to prepare their own meals, and cozy living spaces great for family gatherings.Stamford is located in a picturesque setting, surrounded by the beauty of nature, which provides ample opportunities for outdoor activities such as hiking and exploring the nearby Green Mountain National Forest. Additionally, local attractions like the charming town of Wilmington and the serene Lake Whitingham are just a short drive away, offering even more options for family-friendly outings.
Are there pet-friendly house rentals in Stamford?
In Stamford, Vermont, there are several pet-friendly house rentals available for travellers looking to enjoy a getaway with their furry companions. Many of these properties offer comfortable amenities such as fully equipped kitchens, spacious living areas, and outdoor spaces where pets can roam freely.The surrounding area provides a picturesque setting with opportunities for outdoor activities, including hiking and exploring the scenic landscapes of the Green Mountains. Travellers can find accommodations that cater to families or groups, often featuring cozy fireplaces and access to nature trails nearby, making it a great destination for both relaxation and adventure.
Are there any remote work holiday rentals in Stamford?
In Stamford, Vermont, there are several holiday rentals suitable for remote work. Many of these accommodations provide essential amenities such as free Wi-Fi, dedicated workspaces, and comfortable desk chairs, ensuring a productive environment for travellers needing to balance work and leisure.The area is known for its serene surroundings, which can enhance focus and creativity. Additionally, the charm of Stamford offers a peaceful retreat, with opportunities for outdoor activities like hiking and exploring the natural beauty of the Green Mountains after work hours. To help narrow your search, insert your dates and apply the "WiFi" filter on Bookabach.
What are popular rental amenities in Stamford?
In Stamford, Vermont, popular holiday rentals often feature amenities that enhance the experience of staying in this picturesque mountain town. Many properties include fireplaces, which create a warm and inviting atmosphere, great for chilly evenings. Kitchens are commonly found in these rentals, allowing guests to prepare their own meals and enjoy dining in comfort. Additionally, decks or patios are typical, providing outdoor spaces to relax and take in the stunning mountain views. Many rentals are also conveniently located near mountain biking trails, making it easy for outdoor enthusiasts to explore the beautiful surroundings.
When is the best time to visit Stamford for a holiday rental?
July is the most popular time to visit Stamford, Vermont, drawing in holidaymakers eager to embrace the beauty of summer in this picturesque New England town. The peak season spans from July to September, where visitors can indulge in a variety of outdoor activities, including hiking, biking, and exploring the charming local shops and eateries. The warm weather, with temperatures typically ranging from 15 to 25 degrees Celsius, provides an ideal climate for enjoying the stunning landscapes that Stamford has to offer.During this peak season, Stamford buzzes with life, making it a great time for travellers. July, in particular, sees a vibrant setting as tourists flock to participate in local festivities and outdoor events, ensuring there's never a dull moment.For those seeking a more budget-friendly experience, consider planning your visit in November. This time of year offers a unique perspective of Stamford, as the town transitions into a quieter phase. Visitors can enjoy the peaceful surroundings and perhaps even witness the first signs of winter's arrival, all while benefiting from lower rental rates.Ultimately, the best time to enjoy Stamford really depends on your travel preferences—whether you're drawn to the lively summer atmosphere or the serene beauty of late autumn.
What are the top attractions in Stamford?
In Stamford, Vermont, visitors can enjoy a range of attractions that highlight the area's natural beauty and outdoor activities. The nearby Green Mountain National Forest offers stunning landscapes with opportunities for hiking, camping, and wildlife viewing, making it ideal for nature enthusiasts. The charming town itself is known for its picturesque rural setting, where you can find lovely walking trails and scenic drives.For those interested in local history, Stamford features quaint architecture and historical sites reflecting its heritage. The community often hosts local events and fairs that provide a glimpse into the culture and traditions of the region. Additionally, the surrounding areas boast various outdoor recreational options, including fishing and winter sports during the colder months.
Are all fees included in the Stamford holiday homes prices shown on Bookabach?
Bookabach provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Stamford holiday homes with parking?
Bookabach offers a wide selection of holiday homes in Stamford with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Stamford holiday homes?
You can find great discounts on holiday homes in Stamford on Bookabach, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Stamford holiday home booking on Bookabach?
To find Stamford holiday rentals with free cancellation, just use Bookabach's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Bookabach makes it easy to book with confidence.
Can I find long-stay holiday homes in Stamford?
A long-stay holiday home in Stamford is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Bookabach?
Bookabach's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Stamford holiday home?
Book your Stamford holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Bookabach booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Stamford?
Prices for holiday homes in Stamford vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Bookabach offers something for every taste and budget, from affordable homes in Stamford to more spacious homes.
What can I expect from Bookabach customer service and Bookabach Care™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, Bookabach Care™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Bookabach customer service is available 24/7 to support you every step of the way. Bookabach also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is Bookabach Care™ and how does it work?
Bookabach's mission is to help guests relax, reconnect, and enjoy precious time together. With Bookabach Care™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Bookabach as a host?
Joining Bookabach as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Bookabach makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Bookabach handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.