Photo by David Cedrone

Dorchester holiday lettings

We found 1,315 holiday rentals — enter your dates for availability

Discover a selection of 32 homes, 72 apartments and other holiday rentals in Dorchester that are perfect for your trip. Whether you're travelling with a group or just with your pet, holiday homes have the best amenities for hanging out with the people that matter most, which might include a garden and Wi-Fi. What you'll find is a property to rent to meet everyone's needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts - Dorchester

Showing deals for:24 Oct - 31 Oct
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Why visit Dorchester

  • Cultural richness: Explore Dorchester's vibrant heritage through its historic colleges, universities, and diverse cultural events.
  • Urban parks: Enjoy outdoor adventures in beautiful parks, perfect for family picnics and leisurely strolls.
  • Stunning coastal views: Visit nearby Weymouth Beach for breathtaking sea views and relaxation by the shore.
  • Welcoming community: Experience the friendly locals and warm atmosphere that make Dorchester feel like home.
  • Variety of accommodations: Choose from charming holiday homes, stylish apartments, or modern condos for a perfect stay.

Popular types of accommodation around Dorchester

If you're contemplating a getaway to Dorchester, you're in for a treat! This charming town offers a variety of popular vacation rentals, including private holiday homes, cosy apartments, and modern condos. Whether you’re searching for spacious house rentals, stylish apartments with multiple bedrooms, or inviting guest houses, you'll find the perfect base for your stay. Let us help you discover the ideal accommodation to make your Dorchester experience unforgettable.

  • Houses: The most sought-after option in Dorchester, offering spacious and comfortable settings for families or groups.
  • Apartments: A popular choice for couples or solo travellers, providing convenient access to local amenities.
  • Condos: A great alternative for those looking for a blend of community living and private space.
  • Cottages: Ideal for a quaint retreat, these charming dwellings offer a cosy escape.
  • House Boats: A unique lodging experience, perfect for those wanting to stay on the water.**

Top attractions near Dorchester

Dorchester offers a delightful blend of cultural, family-friendly, and city-themed experiences perfect for any traveller. Explore the urban parks, historic colleges and universities, and vibrant event venues that showcase the area's rich heritage. Whether you're seeking outdoor adventures or cultural insights, Dorchester provides a variety of attractions to make your visit memorable.

  • Fenway Park: A historic sports stadium steeped in baseball culture, Fenway Park offers an electric atmosphere for sports enthusiasts. Just 1.9km from Dorchester, you can immerse yourself in the tradition of America's pastime while enjoying the vibrant local spirit.
  • TD Garden: Located 2.5km from Dorchester, TD Garden serves as a premier venue for major events and conferences. With its dynamic business vibes, it’s a hub for entertainment and sports, making it a must-visit for any visitor to Boston.
  • Boston Common: This expansive urban park, situated 2.5km from Dorchester, is perfect for families and outdoor lovers. Boston Common offers beautifully landscaped areas, walking paths, and a lively city atmosphere, ideal for a relaxing day out.

Things to do recommended for couples

For a romantic getaway in Dorchester, explore the vibrant House of Blues just 1.9km away for live music, or enjoy the cultural charm at the Roxbury Center for Arts, a mere mile from your stay. Don't miss the exhilarating Blue Hills Ski Area, 3.7km away, for some fun on the slopes.

Things to do recommended for families

Families visiting Dorchester can experience the excitement of Agganis Arena, enjoy the serene atmosphere at Larz Anderson Park, and explore the captivating Charles Hayden Planetarium, all within a short distance. These attractions offer a delightful mix of sports, relaxation, and entertainment for a memorable day out.

Things to do recommended for groups

Explore Faneuil Hall Marketplace for a vibrant shopping experience, visit the Samuel Adams Brewery for a taste of local brews, and enjoy a show at the Wilbur Theatre, all within a short distance from Dorchester. These activities promise entertainment and memorable moments for your group.

What do I need to keep in mind when booking a vacation around Dorchester

If you're travelling with a group, as a family, with your pets, or seeking extended stays, it's important to apply the right filters to match your priorities. Here are some helpful Vrbo booking tips for you.

  • Traveling to Dorchester with a group: Think about how many bedrooms you require, along with features like a fully-equipped kitchen or outdoor space for group gatherings. Thankfully, you can easily refine your search for all of these options and more on Vrbo.
  • Traveling to Dorchester with young kids: Journeying with young children can present its difficulties. It's essential to prioritise their comfort and safety, alongside suitable facilities like a private swimming pool. Additionally, it's wise to think about how close you are to attractions that cater to families.
  • Taking your pets with you to Dorchester: For many families, a holiday isn't truly fulfilling unless their furry companions are included. If this resonates with you, explore Vrbo properties that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone can feel completely at home.
  • Planning for a long term stay visiting Dorchester: If you're in search of holiday rentals offering discounts for stays of a month or more, you've come to the perfect spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay near Dorchester

Embarking on a holiday in Dorchester, Boston offers an enriching blend of culture and family-friendly experiences. This vibrant neighbourhood allows visitors to explore the historical charm of the area while enjoying the urban atmosphere. Nearby attractions like Weymouth Beach provide stunning sea views and opportunities for relaxation. With friendly locals and a welcoming vibe, Dorchester is the ideal base for discovering the delightful Dorset coast and its picturesque surroundings.

  • Boston: Boston is a vibrant metropolis located a mere 2.5km from Dorchester. This historic city is a cultural hub, attracting visitors with its rich heritage, diverse arts scene, and family-friendly activities. You can explore iconic landmarks such as the Freedom Trail, catch a concert at the renowned TD Garden, or indulge in shopping at the bustling malls. With a plethora of educational institutions and historic sports venues, Boston offers an enriching travel experience that combines city life with a strong sense of history.
  • Downtown Boston: Situated just 2.5km from Dorchester, Downtown Boston is the heart of the city, brimming with energy and excitement. This neighbourhood is ideal for those seeking a blend of culture and family-oriented experiences. Stroll through the vibrant streets filled with shops, dine at chic restaurants, or visit historic sites like the Boston Common. With easy access to major event venues and sports stadiums, Downtown Boston provides a lively atmosphere perfect for both leisure and entertainment.
  • Meeting House Hill: Meeting House Hill is a charming neighbourhood located only 124m away from Dorchester. This area offers a unique cultural experience with its historic charm and community feel. Visitors can enjoy local shopping centres and educational facilities, making it a great spot for families. The proximity to historic colleges and sports venues adds to its appeal, allowing for leisurely exploration and a taste of local life. Meeting House Hill is perfect for those wanting to experience a friendly, residential vibe while still being close to the city's attractions.

Best time to go to Dorchester

If you're planning a trip to Dorchester, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs from July to September, while off-peak times, like May, October and December tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January30.0°F (-1.1°C)Light RainMostly SunnyAverageSlightly Low
February31.5°F (-0.3°C)Light RainMostly CloudyAverageSlightly Low
March37.9°F (3.3°C)Light RainMostly SunnyAverageSlightly Low
April48.2°F (9.0°C)Light RainMostly SunnyAverageAverage
May58.5°F (14.7°C)Light RainMostly SunnySlightly LowAverage
June66.6°F (19.2°C)Light RainMostly SunnyAverageAverage
July73.6°F (23.1°C)Light RainMostly SunnySlightly HighSlightly High
August72.7°F (22.6°C)Light RainMostly SunnySlightly HighSlightly High
September65.7°F (18.7°C)Light RainMostly SunnySlightly HighAverage
October55.6°F (13.1°C)Light RainMostly SunnySlightly LowSlightly High
November44.4°F (6.9°C)Light RainMostly SunnyAverageAverage
December36.3°F (2.4°C)Light RainMostly SunnySlightly LowAverage

Booking with Vrbo is a breeze

Are you hoping to save on your next holiday? Being flexible with your travel dates can really help, as prices tend to vary. Additionally, opting for a longer stay often leads to significant savings. To discover the perfect Vrbo accommodation that fits your budget, take advantage of our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Effortless planning

Vrbo's innovative Trip Board offers you a dedicated space to plan new getaways, pick up where you last paused, or review and organise your travel arrangements. You can easily access properties you've saved or booked in the sections for Potential, Upcoming, or Current Trips. To make the most of Trip Boards, simply visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

What is the most popular type of holiday rental accommodation in Dorchester?
The most sought-after types of holiday rentals in Dorchester are apartments. Prefer something different? Vrbo has many options to match our guests' requirements, so you'll see holiday homes in loads of shapes and sizes. The ideal home away from home is waiting for you — book yours today.
How much does it cost to rent a holiday rental in Dorchester?
The average price for a holiday home in Dorchester is determined by several factors, including property type, length of stay and time of year. Whether you're thinking about a sprawling villa with space for extended family or a cosy condo perfect for just you and the kids, just enter your travel dates to view stays with terrific value.
How much does it cost to rent a beach house in Dorchester?
When you travel and the style and size of the property will influence how much you'll pay for your beachside stay. Click on your Dorchester travel dates to see all your options on Vrbo. Did someone just say "private pool"? Use the filters to select the features and amenities you need.
Are there pet-friendly holiday rentals in Dorchester?
Pack a travel bag and a bone for your puppy dog because Dorchester has 47 holiday homes that put out the welcome mat to pets. Let your happy hound have fun with the family at one of our pet-friendly holiday rentals on Vrbo. Simply enter your dates and destination, then check the "Pets allowed" filter box.
Can I rent a house with a pool in Dorchester?
Add a whole new level of fun to your trip by booking one of the five houses with a private pool in Dorchester. Use our search filter to find properties with pools on Vrbo, then spend carefree days splish-splashing around in a swimming pool that's just for you.
What are popular rental amenities in Dorchester?
When it comes to rental amenities that guests are looking for in Dorchester, nearby museums, a swimming pool and a nearby waterfront are the most popular. With Vrbo holiday homes, you'll enjoy choices to suit your taste and style, whether you're on a trip with family members, friends or even pets.
Are there large group holiday rentals in Dorchester?
With eight properties that can host 10 or more guests in Dorchester, you won't have to cross anyone off the invite list. From extended family holidays to events like Christmas and birthday parties, Vrbo will help you find a large group rental that fits the occasion.
Are there holiday rentals in Dorchester that welcome kids?
Bring the whole group together for fun-filled adventures in Dorchester at one of our 46 family-friendly holiday homes. These stays come with conveniences that are just perfect for getaways with the little ones, including full kitchens, extra bedrooms and entertainment units. Simply click on the "Properties good for families" filter box and pick out your favourite.
What are the top attractions for families in Dorchester?
Keeping the kids entertained during your stay in Dorchester is simple with these family-friendly attractions:

  • New England Aquarium
  • Museum of Science
  • Boston Tea Party Ship

Are there one-bedroom holiday rentals in Dorchester?
You'll find 16 one-bedroom properties in Dorchester to choose from. A one-bedroom holiday home is an excellent option if it's only two of you or if you're travelling on your own. Throw in more convenience, space and privacy compared to a hotel, and you're sure to have an unforgettable getaway.
Can I find two-bedroom holiday rentals in Dorchester?
Dorchester has 11 two-bedroom holiday properties that you can choose from. Book a holiday home with all the comfort and privacy you want at a price that's hard to resist on Vrbo.
Are there holiday rentals with WiFi in Dorchester?
Whether you'd like to stay in touch with the news, make a video call or update your social media, there are 13 holiday homes with WiFi in Dorchester. Check the "WiFi" box when searching on Vrbo and stay connected on your holiday.
How can I find holiday rentals with air conditioning in Dorchester?
Decide on your travel dates and then use the filters to view holiday rentals with air conditioning in Dorchester on Vrbo. With 44 air-conditioned properties available here, you can enjoy a cool and comfortable trip.
How old do you have to be to rent a holiday rental in Dorchester?
The minimum age requirements can differ between properties on Vrbo, so check the rules of the holiday home in Dorchester you want to book. But in general, it's 16, 18 or 21.
How long can I rent a holiday rental in Dorchester for?
The amount of time you can stay in a Dorchester holiday rental for depends on the property. Just enter your travel dates to find options offering extended stays. They feature the things you need to make your extended getaway more comfortable and convenient, such as kitchens and air conditioning. Some Vrbo holiday homes may also offer discounted weekly or monthly prices, so you can have a longer stay for less.

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