New England is a treasure trove of quaint small towns, each brimming with history, charm, and hospitality. Among its rolling hills, rugged coastlines, and picturesque valleys, you’ll find historic inns and bed & breakfasts that offer a cozy retreat from the hustle and bustle of everyday life. These establishments provide comfortable lodging and serve as gateways to the rich local culture and scenic beauty that define the region. Whether you’re a history buff, a nature enthusiast, or simply searching for a peaceful getaway, these towns offer an authentic New England experience that’s hard to find anywhere else.
20. Chester, Connecticut
Nestled in the heart of the Connecticut River Valley, Chester exudes small-town charm with its tree-lined streets and historic architecture. This picturesque town is home to quaint inns that offer a warm welcome and a taste of local hospitality. Visitors can explore the vibrant arts scene, browse unique boutiques, and enjoy farm-to-table dining in cozy restaurants. Outdoor enthusiasts will appreciate the nearby hiking trails and the scenic river views, making Chester a delightful destination for those seeking relaxation and recreation. For those considering a home in Chester, 3-4 bedroom houses are priced between $400,000 and $463,000, offering an affordable gateway to the town’s charm.
Where is Chester, Connecticut?
Chester is located in Middlesex County, along the western bank of the Connecticut River. Its position in the river valley provides stunning natural landscapes that change beautifully with the seasons. The town is easily accessible via Route 9 and is approximately a two-hour drive from both New York City and Boston. The Chester-Hadlyme Ferry offers a charming crossing of the Connecticut River, connecting visitors to other historic towns and attractions in the region.
19. New Castle, New Hampshire
Perched on a small island off the coast, New Castle is New Hampshire’s easternmost town and a hidden gem brimming with colonial history. The town’s historic inns offer a serene retreat surrounded by ocean views and well-preserved 17th-century architecture. Visitors can stroll through quiet streets, visit the historic Fort Constitution, and enjoy the peaceful ambiance of this coastal enclave. The combination of maritime heritage and natural beauty makes New Castle ideal for a relaxing getaway. Homebuyers looking for 3-4 bedroom properties will find prices ranging from $2,191,000 to $3,106,000, reflecting the area’s exclusivity and coastal appeal.
Where is New Castle, New Hampshire?
New Castle is located just east of Portsmouth, connected to the mainland by bridges over the Piscataqua River. This island town is accessible via Route 1B and is only an hour’s drive north of Boston. Its coastal location provides easy access to nearby beaches, lighthouses, and ocean vistas. The proximity to Portsmouth allows visitors to enjoy the amenities of a larger city while retreating to the tranquility of New Castle’s historic inns by the sea.
18. Wethersfield, Connecticut
Known as Connecticut’s oldest town, Wethersfield offers a rich tapestry of colonial history and charm. The streets are lined with beautifully preserved 18th-century homes, many of which have been converted into inviting bed and breakfasts. Guests can immerse themselves in the past by visiting the Wethersfield Historical Society, exploring the Webb-Deane-Stevens Museum, or taking leisurely walks through the historic district. The town’s commitment to preserving its heritage makes it a captivating destination for history enthusiasts. For prospective residents, 3-4 bedroom homes in Wethersfield are priced between $340,000 and $385,000, offering historical character at an accessible price.
Where is Wethersfield, Connecticut?
Wethersfield is situated just south of Hartford, along the Connecticut River. Its convenient location near Interstate 91 makes it easily accessible from major cities like New York and Boston. The town’s riverfront setting offers picturesque views and opportunities for boating and fishing. Visitors can reach Wethersfield via a short drive from Hartford’s Bradley International Airport, making it a convenient yet serene escape.
17. Brattleboro, Vermont
Brattleboro is a vibrant town known for its artistic community and historic accommodations that reflect its creative spirit. The downtown area is filled with galleries, bookstores, and cafes that showcase local talent and craftsmanship. Historic inns and bed and breakfasts provide a cozy stay with a touch of New England charm. Visitors can enjoy the Brattleboro Museum & Art Center or catch performances at the New England Youth Theatre, making it a cultural haven in the Green Mountain State. For homebuyers, 3-4 bedroom properties in Brattleboro are priced between $308,000 and $325,000, making it an attractive option for a cultural and affordable lifestyle.
Where is Brattleboro, Vermont?
Located in southeastern Vermont, Brattleboro is on the banks of the Connecticut River at the Vermont and New Hampshire border. It is accessible via Interstate 91, making it an easy drive from cities like Boston and Hartford. Surrounded by rolling hills and lush forests, Brattleboro offers outdoor activities like hiking and skiing in nearby locations. The Amtrak Vermonter line also serves the town, providing scenic train travel through the region.
16. Kennebunk, Maine
Kennebunk is a charming town known for its historic homes and cozy inns that capture the essence of New England’s coastal living. The town’s Lower Village and historic district feature beautifully preserved 18th and 19th-century architecture. Visitors can explore the Brick Store Museum, take a scenic stroll along the Kennebunk River, or relax on the sandy beaches nearby. The friendly community and serene atmosphere make Kennebunk a welcoming destination for a peaceful retreat. For those considering a home in Kennebunk, 3-4 bedroom houses are priced between $595,000 and $797,000, reflecting its blend of coastal beauty and historic charm.
Where is Kennebunk, Maine?
Kennebunk is located in York County, along Maine’s southern coast. It’s accessible via Interstate 95 and just a 30-minute drive south of Portland. The town is adjacent to Kennebunkport, which offers additional attractions and dining options. Kennebunk’s coastal location provides ample opportunities for whale watching, sailing, and enjoying fresh seafood. The Portland International Jetport is the nearest airport, offering convenient access for travelers.
15. Littleton, New Hampshire
Nestled in the heart of the White Mountains region, Littleton is a mountain town that blends natural beauty with historic charm. The town’s quaint downtown features historic bed and breakfasts, unique shops, and eateries that cater to visitors year-round. Outdoor enthusiasts can explore nearby attractions like Franconia Notch State Park and Mt. Washington. Littleton’s friendly atmosphere and picturesque surroundings make it a delightful base for mountain adventures. For those considering making Littleton their home, 3-4 bedroom properties are priced between $299,000 and $340,000, offering an affordable option for mountain living.
Where is Littleton, New Hampshire?
Littleton is located in Grafton County, near the northern end of the White Mountains. Accessible via Interstate 93 and Route 302, the town is about a two-and-a-half-hour drive from Boston. Its proximity to major ski resorts and hiking trails makes it an ideal location for outdoor activities in all seasons. The scenic drives around Littleton offer breathtaking views of the mountains and valleys that define this region of New Hampshire.
14. Boothbay Harbor, Maine
Boothbay Harbor offers seaside bliss with its stunning coastal landscapes and quaint bed and breakfasts overlooking the bay. The town is known for its maritime heritage, lobster boats, and the famous Coastal Maine Botanical Gardens. Visitors can embark on whale-watching cruises, explore art galleries, or simply enjoy the fresh sea air from the comfort of a historic inn. Boothbay Harbor’s charm lies in its natural beauty and warm hospitality. Prospective homeowners will find 3-4 bedroom homes priced between $538,000 and $703,000, capturing the essence of coastal Maine living.
Where is Boothbay Harbor, Maine?
Situated on a peninsula in Lincoln County, Boothbay Harbor is accessible via Route 27, about an hour’s drive northeast of Portland. The town’s coastal location provides easy access to kayaking, sailing, and other water activities. Visitors can also explore nearby islands via ferry services. The Portland International Jetport is the closest major airport, making Boothbay Harbor a convenient seaside escape for travelers.
13. Bristol, Rhode Island
Bristol is a waterfront town that exudes coastal serenity with its historic bed and breakfasts and tree-lined streets. Known for its patriotic Fourth of July celebrations, Bristol offers a rich blend of history and community spirit. Visitors can explore the Blithewold Mansion, Gardens & Arboretum or walk along the East Bay Bike Path. The town’s harbor views and friendly atmosphere make it a charming destination for a relaxing stay. Homebuyers looking for 3-4 bedroom properties in Bristol will find prices ranging from $605,000 to $680,000, reflecting the town’s coastal appeal.
Where is Bristol, Rhode Island?
Bristol is located on a peninsula between Narragansett Bay and Mount Hope Bay in the eastern part of Rhode Island. It’s accessible via Route 114 and is approximately a 30-minute drive from Providence. The town’s coastal setting offers picturesque views and maritime activities. Nearby attractions include Colt State Park and access to ferry services to Prudence Island, enhancing Bristol’s appeal as a waterfront getaway.
12. Newfane, Vermont
Experience the quintessential New England village in Newfane, where historic greens and charming inns create an idyllic setting. The town is renowned for its well-preserved Federal and Greek Revival architecture. Visitors can enjoy antique shopping, local art galleries, and seasonal farmers’ markets. The peaceful rural atmosphere makes Newfane an excellent choice for those seeking a quiet escape in a picturesque environment. For those interested in settling down, 3-4 bedroom homes in Newfane are priced between $379,000 and $650,000, offering a mix of charm and affordability.
Where is Newfane, Vermont?
Newfane is located in Windham County, southeastern Vermont. It’s just a short drive north of Brattleboro, accessible via Route 30. The town is surrounded by rolling hills and scenic byways, offering beautiful landscapes, especially during the fall foliage season. The area also offers opportunities for hiking, skiing, and exploring covered bridges, adding to its rural charm.
11. Ogunquit, Maine
Ogunquit, meaning “beautiful place by the sea,” lives up to its name with coastal trails and historic bed and breakfasts. Visitors can walk the famed Marginal Way, a scenic cliffside path offering stunning ocean views. The town boasts a vibrant arts scene with the Ogunquit Playhouse and numerous galleries. Staying in one of the historic B&Bs allows guests to immerse themselves in the seaside ambiance and enjoy fresh local seafood. For potential residents, 3-4 bedroom homes in Ogunquit range from $1,045,000 to $1,343,000, reflecting its status as a luxurious seaside retreat.
Where is Ogunquit, Maine?
Located in York County along Maine’s southern coast, Ogunquit is accessible via Route 1, just over an hour’s drive north of Boston. The town’s coastline features sandy beaches and dramatic cliffs. Nearby, visitors can explore Perkins Cove and take boat tours along the coast. The Portland International Jetport and Boston’s Logan Airport provide convenient options for travelers flying into the region.
10. Stockbridge, Massachusetts
Visit the town that inspired Norman Rockwell’s iconic paintings, staying in charming lodgings that reflect Stockbridge’s timeless appeal. The town is home to the Norman Rockwell Museum, where visitors can view an extensive collection of his works. Historic inns offer a cozy retreat amid the Berkshires’ scenic beauty. Guests can explore boutique shops, dine in local restaurants, and enjoy outdoor activities like hiking and golfing. For those considering a home in Stockbridge, 3-4 bedroom properties are priced between $676,000 and $894,000, reflecting the town’s blend of culture and scenic surroundings.
Where is Stockbridge, Massachusetts?
Stockbridge is located in Berkshire County, western Massachusetts. It is accessible via Interstate 90 and Route 7 and is approximately a two-hour drive from Boston and New York City. The town’s location in the Berkshire Mountains makes it a popular destination for leaf-peeping in the fall. Nearby attractions include Tanglewood and the Berkshire Botanical Garden, which provide cultural and natural experiences for visitors.
9. Essex, Connecticut
Stroll along the Connecticut River in Essex and stay in historic inns that echo the town’s maritime legacy. Essex is famed for its well-preserved downtown, featuring colonial and Federal-style architecture. Visitors can explore the Connecticut River Museum, enjoy riverboat cruises, or attend the annual Burning of the Ships Festival. The town’s serene environment and rich history make it a captivating destination. For potential homeowners, 3-4 bedroom houses in Essex are priced between $595,000 and $760,000, offering a taste of New England charm.
Where is Essex, Connecticut?
Essex is located in Middlesex County along the Connecticut River, accessible via Route 9. It’s approximately a 45-minute drive south of Hartford. The town’s riverfront location offers scenic views and opportunities for water activities. Visitors can also take the Essex Steam Train for a nostalgic journey through the Connecticut River Valley. The town’s accessibility and charm make it a desirable spot for travelers seeking a historic experience.
8. Chester, Vermont
Discover the tranquil village of Chester, with its historic inns set amidst classic New England architecture. The town is known for its Stone Village Historic District, featuring unique stone houses built in the 19th century. Visitors can browse antique shops and art galleries, and enjoy local cuisine in cozy eateries. The peaceful ambiance and friendly community make Chester an inviting destination for relaxation and exploration. Prospective residents will find 3-4 bedroom homes in Chester priced between $578,000 and $652,000, combining rural charm with historical allure.
Where is Chester, Vermont?
Chester is located in Windsor County, accessible via Routes 103 and 11. It’s about a two-hour drive from Boston and Albany. Surrounded by the Green Mountains, the town offers easy access to outdoor activities like skiing at nearby Okemo Mountain Resort and hiking in state forests. The picturesque landscapes and convenient location make Chester a charming spot for visitors year-round.
7. Rockport, Massachusetts
Explore the artistic haven of Rockport, staying in quaint bed and breakfasts near its picturesque harbor and galleries. The town is home to Motif No. 1, a famous red fishing shack that has been the subject of countless paintings and photographs. Visitors can wander through Bearskin Neck, a collection of shops and studios along the waterfront. Rockport’s coastal scenery and vibrant arts community create an enriching experience for guests. For those interested in settling down, 3-4 bedroom homes in Rockport are priced between $772,000 and $984,000, providing access to its unique coastal and cultural lifestyle.
Where is Rockport, Massachusetts?
Rockport is located on Cape Ann in Essex County, accessible via Route 127. It’s about an hour’s drive northeast of Boston. The town’s coastal position offers beautiful beaches and rocky shores, perfect for sightseeing and relaxation. The MBTA commuter rail provides service from Boston to Rockport, making it an easy day trip or weekend getaway. Its proximity to Gloucester also allows visitors to enjoy whale-watching excursions.
6. Lenox, Massachusetts
Immerse yourself in the cultural richness of Lenox, home to the renowned Tanglewood Music Center, and relax in its stately historic inns. The town offers a blend of artistic attractions, including The Mount, Edith Wharton’s estate, and several art galleries. Visitors can enjoy performances by the Boston Symphony Orchestra during the summer season. Lenox’s charming downtown features boutique shopping and fine dining, making it a sophisticated retreat. Homebuyers in Lenox can expect 3-4 bedroom homes to be priced between $623,000 and $985,000, offering a luxurious lifestyle amidst the Berkshires’ natural beauty.
Where is Lenox, Massachusetts?
Lenox is situated in the Berkshires of western Massachusetts, accessible via Interstate 90 and Routes 7 and 20. It’s approximately two and a half hours from New York City and Boston. The town’s location provides easy access to outdoor activities like hiking, skiing, and exploring the surrounding mountains. Nearby airports include Albany International Airport and Bradley International Airport in Hartford, offering convenient travel options.
5. Stowe, Vermont
Enjoy the stunning mountain vistas of Stowe while staying in historic lodgings that capture the town’s rustic charm. Known as a premier ski destination, Stowe offers year-round activities, including hiking, biking, and exploring waterfalls. The historic downtown features shops, galleries, and restaurants that highlight local artisans and cuisine. Staying in a historic inn allows guests to experience the town’s warm hospitality and picturesque surroundings. For those interested in making Stowe home, 3-4 bedroom properties are priced between $996,000 and $1,331,000, offering mountain living with all the charm of a resort destination.
Where is Stowe, Vermont?
Stowe is located in Lamoille County, in north-central Vermont. Accessible via Interstate 89 and Route 100, it’s about a three-hour drive from Boston and a two-hour drive from Montreal. The town is nestled at the base of Mount Mansfield, Vermont’s highest peak. Burlington International Airport is the nearest major airport, providing easy access for travelers. The scenic routes to Stowe offer breathtaking views of Vermont’s natural beauty.
4. Mystic, Connecticut
Uncover the nautical past of Mystic while staying in cozy bed and breakfasts near the famed Mystic Seaport and charming downtown. The Mystic Seaport Museum offers a glimpse into maritime history with historic ships and interactive exhibits. Visitors can also explore the Mystic Aquarium or enjoy shopping and dining in Olde Mistick Village. The town’s coastal charm and rich heritage make it an engaging destination for all ages. For those seeking to settle in Mystic, 3-4 bedroom homes range from $735,000 to $1,100,000, reflecting the town’s blend of history and coastal living.
Where is Mystic, Connecticut?
Mystic is located in Groton and Stonington along the Mystic River, accessible via Interstate 95. It’s approximately halfway between New York City and Boston, making it an ideal stop along the Northeast Corridor. The town’s coastal location provides opportunities for sailing and waterfront activities. Amtrak services the nearby New London station, offering additional travel convenience for visitors.
3. Kennebunkport, Maine
Delve into the maritime history of Kennebunkport while staying in its charming historic inns and exploring its scenic coastline. The town is famous for its picturesque Dock Square, which is lined with shops, galleries, and restaurants. Visitors can tour the historic Bush family compound at Walker’s Point or enjoy a lobster boat tour. Kennebunkport’s blend of luxury accommodations and coastal beauty offers a quintessential New England experience. For prospective homeowners, 3-4 bedroom houses in Kennebunkport are priced between $929,000 and $1,298,000, offering access to its elegant coastal lifestyle.
Where is Kennebunkport, Maine?
Kennebunkport is situated along Maine’s southern coast in York County, accessible via Interstate 95 and Route 9. It’s about a 90-minute drive north of Boston. The town’s coastal setting provides beautiful beaches, lighthouses, and maritime activities. The Portland International Jetport is the nearest major airport, with shuttle services and car rentals available for travelers continuing to Kennebunkport.
2. Woodstock, Vermont
Experience the classic New England ambiance of Woodstock, where historic bed and breakfasts are nestled among covered bridges and rolling hills. The town features the Billings Farm & Museum, offering insights into Vermont’s agricultural history. Visitors can explore artisan shops and galleries, and enjoy locally sourced dining options. Woodstock’s charming village green and historic sites make it a picturesque and inviting destination. Those looking to call Woodstock home will find 3-4 bedroom homes priced between $1,454,000 and $2,157,000, providing a premium location surrounded by natural beauty.
Where is Woodstock, Vermont?
Woodstock is located in Windsor County, accessible via Interstate 89 and Route 4. It’s roughly a two-and-a-half-hour drive from Boston and about an hour from Burlington. The town’s location provides access to outdoor activities like hiking in the Marsh-Billings-Rockefeller National Historical Park and skiing at nearby Killington Resort. The Lebanon Municipal Airport in New Hampshire is the closest airport for regional flights.
1. Camden, Maine
Discover the seaside allure of Camden, a picturesque town with historic inns offering stunning harbor views and a vibrant local culture. Known as the “Jewel of the Maine Coast,” Camden offers opportunities to sail aboard historic schooners, hike in Camden Hills State Park, and enjoy performances at the Camden Opera House. The scenic beauty and warm hospitality of Camden’s bed and breakfasts make it the perfect destination for a coastal retreat. For those seeking to live in Camden, 3-4 bedroom homes are priced between $643,000 and $797,000, offering a blend of coastal living and small-town charm.
Where is Camden, Maine?
Camden is located in Knox County along Penobscot Bay, accessible via Route 1. It’s approximately a two-hour drive northeast of Portland. The town’s harbor is a focal point, offering panoramic views and access to the bay’s islands. Visitors can fly into the Knox County Regional Airport or the Portland International Jetport and enjoy a scenic drive along Maine’s rugged coastline to reach Camden. The town’s stunning geography and easy accessibility make it a must-visit destination in New England.
