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Westport Rentals

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Results: 34 Rentals

  • Westport: Walk to Town, Private Natural Setting, Lovely Neighborhood
    From $808 per night (USD)

    VRBO

    Westport: Walk to Town, Private Natural Setting, Lovely Neighborhood

    Bedrooms:
    2
    Bathrooms:
    5
    Sleeps:
    8

    Beautiful neighborhood close to town. Walk to restaurants, town tennis courts. One floor living. Wheels2U, a town spon ...

    From $808 per night (USD)

    VRBO

    Details
  • 3 Bedroom Luxury Cape - Walk To Train & Beach
    From $377 per night (USD)

    VRBO

    3 Bedroom Luxury Cape - Walk To Train & Beach

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Our home was recently renovated. In addition to high end finishes, there are 3 bedrooms that comfortably sleep 6. There ...

    From $377 per night (USD)

    VRBO

    Details
  • Fabulous private home on desirable street in Westport.
    From $988 per night (USD)

    VRBO

    Fabulous private home on desirable street in Westport.

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    6

    Our wonderful home is light filled, private yet near everything, with a beautiful deck, gazebo and plenty of space to re ...

    From $988 per night (USD)

    VRBO

    Details
  • Newly Renovated Home in Westport CT, Private Pool, Walk to Town, Close to Beach
    From $1214 per night (USD)

    Expedia

    Newly Renovated Home in Westport CT, Private Pool, Walk to Town, Close to Beach

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    10

    This newly renovated home is being offered for a summer rental. This light and airy 3 bedroom, 2.5 bath with dream kitch ...

    From $1214 per night (USD)

    Expedia

    Details
  • Modern Farmhouse
    From $983 per night (USD)

    VRBO

    Modern Farmhouse

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    Outside - 1 Mile to town - 10 minutes (2 miles) to beach and golf course - Private setting - Porch with couch - Big ...

    From $983 per night (USD)

    VRBO

    Details
  • Historic oyster shack.
    From $4624 per night (USD)

    VRBO

    Historic oyster shack.

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    10

    Picturesque New England oyster farm cottage on a private island overlooking an intertidal salt pond. Built in the 1700s ...

    From $4624 per night (USD)

    VRBO

    Details
  • Luxury Westport Retreat | Resort Pool + Spa | Near Compo Beach
    From $876 per night (USD)

    VRBO

    Luxury Westport Retreat | Resort Pool + Spa | Near Compo Beach

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    5

    Summary: Welcome to The Styled Stay Westport, a thoughtfully designed luxury retreat where elevated interiors meet reso ...

    From $876 per night (USD)

    VRBO

    Details
  • DIRECT WATERFRONT Westport Beachhouse!
    From $948 per night (USD)

    VRBO

    DIRECT WATERFRONT Westport Beachhouse!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    3

    Quintessential New England Beach Cottage DIRECT waterfront and just 1 mile to the Westport train station, great restaura ...

    From $948 per night (USD)

    VRBO

    Details
  • Summer rental House Westport
    From $419 per night (USD)

    VRBO

    Summer rental House Westport

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Stunning three bedroom house with Dining Room, Living Roomon on a private road, one mile from beach, near town center, ...

    From $419 per night (USD)

    VRBO

    Details
  • Historic Loft, Co-Work, River View
    From $240 per night (USD)

    Expedia

    Historic Loft, Co-Work, River View

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    Unique studio loft in a beautifully restored 19th-century Cider Mill on the Westport/Southport border. Enjoy picturesque ...

    From $240 per night (USD)

    Expedia

    Details
  • Nama-stay, sweet pink Saugatuck Shores beach cottage
    From $668 per night (USD)

    VRBO

    Nama-stay, sweet pink Saugatuck Shores beach cottage

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    4

    Escape to our beautifully curated pink beach cottage in the exclusive Saugatuck Shores neighborhood of Westport, Connect ...

    From $668 per night (USD)

    VRBO

    Details
  • STUNNING POOL & SCREENED PORCH! Private home, close to EVERYTHING!!
    From $1038 per night (USD)

    VRBO

    STUNNING POOL & SCREENED PORCH! Private home, close to EVERYTHING!!

    Bedrooms:
    2
    Bathrooms:
    5
    Sleeps:
    9

    Charming Colonial home in a fabulous Westport location. Two minutes from Post Road and 5 minutes to Compo Beach. House ...

    From $1038 per night (USD)

    VRBO

    Details
  • Designer Modern Westport Estate
    From $3775 per night (USD)

    VRBO

    Designer Modern Westport Estate

    Bedrooms:
    7
    Bathrooms:
    5
    Sleeps:
    12

    Built in 2022, this custom designer 5 bedroom, 7 bathroom estate is located in the heart of Westport, CT, Greens Farms a ...

    From $3775 per night (USD)

    VRBO

    Details
  • Chic, Impeccably Decorated 5000 sq ft Estate, Coveted Greens Farms, 5 bed, 6 bth
    From $1655 per night (USD)

    VRBO

    Chic, Impeccably Decorated 5000 sq ft Estate, Coveted Greens Farms, 5 bed, 6 bth

    Bedrooms:
    5
    Bathrooms:
    5
    Sleeps:
    8

    Westport Perfection. One of the most desirable homes in Westport situated on one acre. Located on one of the best street ...

    From $1655 per night (USD)

    VRBO

    Details
  • 2BR Flat above Historic Cider Mill
    From $296 per night (USD)

    VRBO

    2BR Flat above Historic Cider Mill

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    Escape to a sun-filled, 2-bedroom artisan retreat in a restored 1850s cider mill. Overlooking a peaceful marsh near West ...

    From $296 per night (USD)

    VRBO

    Details
  • Farmhouse 1899: Westport, CT - Minutes to Downtown, family and pet-friendly.
    From $941 per night (USD)

    VRBO

    Farmhouse 1899: Westport, CT - Minutes to Downtown, family and pet-friendly.

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    9

    Welcome to Farmhouse 1899. This old house is full of charm and history and is the perfect mix of old and new. Every inch ...

    From $941 per night (USD)

    VRBO

    Details
  • Westport Gem - walk to shops, dining, town center, pet-friendly
    From $586 per night (USD)

    VRBO

    Westport Gem - walk to shops, dining, town center, pet-friendly

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Looking for a great deal? Discounts are automatically applied based on your length of stay! No need for promo codes or r ...

    From $586 per night (USD)

    VRBO

    Details
  • The Riverside
    From $307 per night (USD)

    VRBO

    The Riverside

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    3

    Enjoy this great-centered location apartment in Downtown Westport. This beautiful, fully renovated apartment is located ...

    From $307 per night (USD)

    VRBO

    Details
  • Spacious Studio with Pool Table
    From $224 per night (USD)

    VRBO

    Spacious Studio with Pool Table

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Summary: Escape to your private Westport studio retreat in one of the most desirable neighborhoods in town! This stylis ...

    From $224 per night (USD)

    VRBO

    Details
  • Westport Family Friendly Oasis
    From $2317 per night (USD)

    VRBO

    Westport Family Friendly Oasis

    Bedrooms:
    5
    Bathrooms:
    6
    Sleeps:
    12

    Be prepared to be wowed! Westport home close to beach. If you are looking for that special place to call "Home", this i ...

    From $2317 per night (USD)

    VRBO

    Details
  • Spacious 6-bedroom 5 bathroom Dream House, with salt water pool & stone hot tub.
    Click For Pricing

    VRBO

    Spacious 6-bedroom 5 bathroom Dream House, with salt water pool & stone hot tub.

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    13

    This stunning house in Westport offers 6 bedrooms, including 3 queen beds, 1 king bed, 1 full bed, 1 bunk bed. Plus ad ...

    Click For Pricing

    VRBO

    Details
  • Boho Chic Private Home in the Heart of Westport CT
    From $509 per night (USD)

    Expedia

    Boho Chic Private Home in the Heart of Westport CT

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    The best of both worlds! Centrally located Westport flat surrounded by greenery and wildlife, tucked in a private neighb ...

    From $509 per night (USD)

    Expedia

    Details
  • Westport Summer retreat -Available 6/21 to 7/6 with saltwater pool, 6bedrooms
    From $2195 per night (USD)

    VRBO

    Westport Summer retreat -Available 6/21 to 7/6 with saltwater pool, 6bedrooms

    Bedrooms:
    6
    Bathrooms:
    6
    Sleeps:
    14

    A Westport summer vacation retreat. The property features a recently built 40 foot saltwater gunite heated pool and spa ...

    From $2195 per night (USD)

    VRBO

    Details
  • Westport Dream Home 6 Bedroom / 5 Bathroom Pool and Jacuzzi Steps to town
    From $2498 per night (USD)

    VRBO

    Westport Dream Home 6 Bedroom / 5 Bathroom Pool and Jacuzzi Steps to town

    Bedrooms:
    5
    Bathrooms:
    6
    Sleeps:
    9

    Unwind in Westport at this dream house. With 6 bedrooms, 5 bathrooms, and a newly put in Salt Water pool, stone Jacuz ...

    From $2498 per night (USD)

    VRBO

    Details
  • Summer, FURNISHED: CENTRAL WESTPORT ESTATE, 60' pool: 2 mins to beach/town/train
    From $2303 per night (USD)

    VRBO

    Summer, FURNISHED: CENTRAL WESTPORT ESTATE, 60' pool: 2 mins to beach/town/train

    Bedrooms:
    5
    Bathrooms:
    7
    Sleeps:
    14

    Summer rental of the most private and central multi-acre estate in Westport, CT - available June-August! Fully furnished ...

    From $2303 per night (USD)

    VRBO

    Details
  • Charming 4-bedroom house with AC and WiFi in fabulous Westport
    From $1046 per night (USD)

    Expedia

    Charming 4-bedroom house with AC and WiFi in fabulous Westport

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    6

    Escape to this serene house in picturesque Westport. With 4 bedrooms including 1 queen bed and 3 full beds, along with 3 ...

    From $1046 per night (USD)

    Expedia

    Details
  • Your Summer Retreat, Modern and Spacious 5-bed house in marvelous Westport, CT!
    From $1207 per night (USD)

    VRBO

    Your Summer Retreat, Modern and Spacious 5-bed house in marvelous Westport, CT!

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    8

    Imaging spending lazy summer days in our Very New (2023), Spacious and luxurious 5-bedroom house in marvelous Westport. ...

    From $1207 per night (USD)

    VRBO

    Details
  • Villa Après Sea
    From $754 per night (USD)

    Expedia

    Villa Après Sea

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Get ready to play with the whole family at this stylish/private/gated 1-acre Gold Coast house equipped w/ a ping-pong ta ...

    From $754 per night (USD)

    Expedia

    Details
  • Spacious 5-bedroom house with waterfall view and walk to town
    From $995 per night (USD)

    VRBO

    Spacious 5-bedroom house with waterfall view and walk to town

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    10

    This 5-bedroom house is perfect for your escape to Westport. Guests will find 3 queen beds, 1 full bed, and 2 twin beds, ...

    From $995 per night (USD)

    VRBO

    Details
  • Cozy Apartment in Downtown Westport
    From $193 per night (USD)

    VRBO

    Cozy Apartment in Downtown Westport

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    This cozy historic home synchronizes the entertainment, calm and beauty of Westport. With one of the best locations in W ...

    From $193 per night (USD)

    VRBO

    Details
  • Tranquil 3-bedroom house with AC in charming Westport, Connecticut
    From $1123 per night (USD)

    VRBO

    Tranquil 3-bedroom house with AC in charming Westport, Connecticut

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    Escape to a charming 4-bedroom house in Westport. Located in the Old Hill District within walking distance to Westports' ...

    From $1123 per night (USD)

    VRBO

    Details
  • Westport Connecticut Greensfarms Road Gated Estate Home Mint Condition
    From $888 per night (USD)

    Expedia

    Westport Connecticut Greensfarms Road Gated Estate Home Mint Condition

    Bedrooms:
    7
    Bathrooms:
    5
    Sleeps:
    10

    Minimum 1 month stay for this Triple Mint Never Available Rental Opportunity In-between homes? Need a short-term fully f ...

    From $888 per night (USD)

    Expedia

    Details
  • New Family Friendly House in Westport
    From $2577 per night (USD)

    VRBO

    New Family Friendly House in Westport

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    10

    Welcome to your ideal getaway at this beautiful house! This charming property offers a perfect blend of comfort and styl ...

    From $2577 per night (USD)

    VRBO

    Details
  • House in Westport, Mid and Long term Available
    From $1325 per night (USD)

    Expedia

    House in Westport, Mid and Long term Available

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    Beautiful Westport Retreat – Minutes to Beach, Town & Train Welcome to your perfect Westport escape. Nestled on a quiet ...

    From $1325 per night (USD)

    Expedia

    Details