Vacation rentals in Round Bay, MD

Best vacation rentals and Airbnb offers in Round Bay, MD

10 ★ 171 reviews

Waterfront Apartment with Fantastic Views

Apartment, Round Bay

Waterfront Apartment with Fantastic Views is a apartment in Round Bay, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Waterfront Apartment with Fantastic Views

Waterfront Apartment with Fantastic Views is a apartment in Round Bay, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,299.

From$186/night

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10 ★ 18 reviews

Annapolis Tree House Apartment- luxury shower, separate space

Apartment, Round Bay

Annapolis Tree House Apartment- luxury shower, separate space is a apartment in Round Bay, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Annapolis Tree House Apartment- luxury shower, separate space

Annapolis Tree House Apartment- luxury shower, separate space is a apartment in Round Bay, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,569.

From$224/night

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10 ★ 16 reviews

Annapolis Garden Suite

Holiday Home, Round Bay

Annapolis Garden Suite is a holiday home in Round Bay, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Annapolis Garden Suite

Annapolis Garden Suite is a holiday home in Round Bay, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, free wifi, pet friendly, and pets friendly.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,050.

From$293/night

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10 ★ 9 reviews

Prime Viewing for Blue Angels -Rooftop Deck and Water Views of Spa Creek!

Condo, Round Bay

Prime Viewing for Blue Angels -Rooftop Deck and Water Views of Spa Creek! is a condo in Round Bay, with pool access, outdoor space, and parking. This stay gives travelers a comfortable base…

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About Prime Viewing for Blue Angels -Rooftop Deck and Water Views of Spa Creek!

Prime Viewing for Blue Angels -Rooftop Deck and Water Views of Spa Creek! is a condo in Round Bay, with pool access, outdoor space, and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, kitchen, with kitchen, and parking.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,671.

From$239/night

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Waterfront vacation rentals in Round Bay, MD

Discover vacation rentals close to the coast, water, and beach areas around Round Bay, MD.

10 ★ 9 reviews

Riverside Retreat ~ Near Annapolis & USNA ~ Home Theatre, Bar & Beach Access

Holiday Home, Round Bay

Riverside Retreat ~ Near Annapolis & USNA ~ Home Theatre, Bar & Beach Access is a holiday home in Round Bay, with easy beach access, parking, and kitchen access. This stay gives travelers a…

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About Riverside Retreat ~ Near Annapolis & USNA ~ Home Theatre, Bar & Beach Access

Riverside Retreat ~ Near Annapolis & USNA ~ Home Theatre, Bar & Beach Access is a holiday home in Round Bay, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,153.

From$308/night

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10 ★ 3 reviews

Renovated 3BR | Near Sandy Point Beach

Holiday Home, Round Bay

Renovated 3BR · Near Sandy Point Beach is a holiday home in Round Bay, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Renovated 3BR | Near Sandy Point Beach

Renovated 3BR · Near Sandy Point Beach is a holiday home in Round Bay, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $3,046.

From$435/night

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10 ★ 2 reviews

Captains Quarters | Waterfront & Pool

Condo, Round Bay

Captains Quarters · Waterfront & Pool is a condo in Round Bay, with pool access, easy beach access, and parking. This stay gives travelers a comfortable base for exploring the area,…

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About Captains Quarters | Waterfront & Pool

Captains Quarters · Waterfront & Pool is a condo in Round Bay, with pool access, easy beach access, and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, kitchen, with kitchen, and parking.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,989.

From$427/night

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9.8 ★ 56 reviews

WATERFRONT COTTAGE ON SEVERN - STUNNING VIEWS - MINUTES FROM DOWNTOWN ANNAPOLIS

Cottage, Round Bay

WATERFRONT COTTAGE ON SEVERN - STUNNING VIEWS - MINUTES FROM DOWNTOWN ANNAPOLIS is a cottage in Round Bay, with pet-friendly space, easy beach access, and kitchen access. This stay gives…

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About WATERFRONT COTTAGE ON SEVERN - STUNNING VIEWS - MINUTES FROM DOWNTOWN ANNAPOLIS

WATERFRONT COTTAGE ON SEVERN - STUNNING VIEWS - MINUTES FROM DOWNTOWN ANNAPOLIS is a cottage in Round Bay, with pet-friendly space, easy beach access, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free wifi, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $4,533.

From$648/night

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Family-friendly vacation rentals in Round Bay, MD

Plan a trip with stays that give families more room to spread out.

10 ★ 59 reviews

Eastport Cottage .5 mi from Downtown Annapolis

Holiday Home, Round Bay

Eastport Cottage .5 mi from Downtown Annapolis is a holiday home in Round Bay, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Eastport Cottage .5 mi from Downtown Annapolis

Eastport Cottage .5 mi from Downtown Annapolis is a holiday home in Round Bay, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,960.

From$423/night

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10 ★ 21 reviews

Game Days & Family Stays at Dog-Friendly Home Near Navy Stadium w Private Fenced-In Yard

Holiday Home, Round Bay

Game Days & Family Stays at Dog-Friendly Home Near Navy Stadium w Private Fenced-In Yard is a holiday home in Round Bay, with pet-friendly space, kitchen access, and room for a group. This…

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About Game Days & Family Stays at Dog-Friendly Home Near Navy Stadium w Private Fenced-In Yard

Game Days & Family Stays at Dog-Friendly Home Near Navy Stadium w Private Fenced-In Yard is a holiday home in Round Bay, with pet-friendly space, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $3,063.

From$438/night

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10 ★ 2 reviews

Annapolis Town Center Cottage

Holiday Home, Round Bay

Annapolis Town Center Cottage is a holiday home in Round Bay, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings,…

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About Annapolis Town Center Cottage

Annapolis Town Center Cottage is a holiday home in Round Bay, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,069.

From$296/night

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9.8 ★ 6 reviews

Waterfront 3br Cottage - Paddle, Fish, Sand, Sun!

Holiday Home, Round Bay

Waterfront 3br Cottage - Paddle, Fish, Sand, Sun! is a holiday home in Round Bay, with easy beach access, kitchen access, and room for a group. This stay gives travelers a comfortable base…

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About Waterfront 3br Cottage - Paddle, Fish, Sand, Sun!

Waterfront 3br Cottage - Paddle, Fish, Sand, Sun! is a holiday home in Round Bay, with easy beach access, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, kids friendly, and kids friendly videos or books.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,862.

From$409/night

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Pet-friendly vacation rentals in Round Bay, MD

Bring your pet along with stays that welcome four-legged travelers.

10 ★ 52 reviews

Waterfront Annapolis w/swimming pool & pier - A Perfect place to Unwind

Holiday Home, Round Bay

Waterfront Annapolis w/swimming pool & pier - A Perfect place to Unwind is a holiday home in Round Bay, with pet-friendly space, pool access, and easy beach access. This stay gives…

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About Waterfront Annapolis w/swimming pool & pier - A Perfect place to Unwind

Waterfront Annapolis w/swimming pool & pier - A Perfect place to Unwind is a holiday home in Round Bay, with pet-friendly space, pool access, and easy beach access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, pet friendly, pets friendly, and kitchen.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $3,051.

From$436/night

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10 ★ 25 reviews

13 Mi to Annapolis: Dog-Friendly Home w/ Fire Pit!

Holiday Home, Round Bay

13 Mi to Annapolis: Dog-Friendly Home w/ Fire Pit! is a holiday home in Round Bay, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About 13 Mi to Annapolis: Dog-Friendly Home w/ Fire Pit!

13 Mi to Annapolis: Dog-Friendly Home w/ Fire Pit! is a holiday home in Round Bay, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,497.

From$357/night

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9.8 ★ 70 reviews

The Very Best location - 50 Steps from Main Street

Holiday Home, Round Bay

The Very Best location - 50 Steps from Main Street is a holiday home in Round Bay, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About The Very Best location - 50 Steps from Main Street

The Very Best location - 50 Steps from Main Street is a holiday home in Round Bay, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, hot tub, kitchen, with kitchen, and washer.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,442.

From$349/night

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8.8 ★ 10 reviews

Glen Burnie Vacation Rental w/ Private Deck!

Holiday Home, Round Bay

Glen Burnie Vacation Rental w/ Private Deck! is a holiday home in Round Bay, with pet-friendly space, outdoor space, and parking. This stay gives travelers a comfortable base for exploring…

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About Glen Burnie Vacation Rental w/ Private Deck!

Glen Burnie Vacation Rental w/ Private Deck! is a holiday home in Round Bay, with pet-friendly space, outdoor space, and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,697.

From$242/night

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Vacation rentals with a pool in Round Bay, MD

Add a pool to the search when you want an easy place to cool off between outings.

10 ★ 95 reviews

Annapolis Entertainment Complex

Holiday Home, Round Bay

Annapolis Entertainment Complex is a holiday home in Round Bay, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending…

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About Annapolis Entertainment Complex

Annapolis Entertainment Complex is a holiday home in Round Bay, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, hot tub, and free wifi.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $5,184.

From$741/night

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10 ★ 27 reviews

BWI, Annapolis, DC, Baltimore, USNA family-sized house with a game room and deck

Holiday Home, Round Bay

BWI, Annapolis, DC, Baltimore, USNA family-sized house with a game room and deck is a holiday home in Round Bay, with pool access, outdoor space, and room for a group. This stay gives…

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About BWI, Annapolis, DC, Baltimore, USNA family-sized house with a game room and deck

BWI, Annapolis, DC, Baltimore, USNA family-sized house with a game room and deck is a holiday home in Round Bay, with pool access, outdoor space, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, hot tub, and free wifi.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $3,220.

From$460/night

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10 ★ 2 reviews

Waterfront Suite with Views of Annapolis, Prime Eastport Location

Condo, Round Bay

Waterfront Suite with Views of Annapolis, Prime Eastport Location is a condo in Round Bay, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable…

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About Waterfront Suite with Views of Annapolis, Prime Eastport Location

Waterfront Suite with Views of Annapolis, Prime Eastport Location is a condo in Round Bay, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, free wifi, kitchen, and with kitchen.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,971.

From$424/night

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8.6 ★ 11 reviews

HiddenParadise in Scenic community, mins to attractions & WaterFront. Sleeps 9

Holiday Home, Round Bay

HiddenParadise in Scenic community, mins to attractions & WaterFront. Sleeps 9 is a holiday home in Round Bay, with pet-friendly space, pool access, and easy beach access. This stay gives…

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About HiddenParadise in Scenic community, mins to attractions & WaterFront. Sleeps 9

HiddenParadise in Scenic community, mins to attractions & WaterFront. Sleeps 9 is a holiday home in Round Bay, with pet-friendly space, pool access, and easy beach access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, free wifi, pet friendly, and pets friendly.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,960.

From$423/night

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Vacation rentals with parking in Round Bay, MD

Find vacation rentals that make arriving by car easier.

10 ★ 21 reviews

Corner House - Cozy Five Star 2 Bedroom Suite. Downtown and Stadium. Parking!

Holiday Home, Round Bay

Corner House - Cozy Five Star 2 Bedroom Suite. Downtown and Stadium. Parking! is a holiday home in Round Bay, with parking, kitchen access, and room for a group. This stay gives travelers a…

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About Corner House - Cozy Five Star 2 Bedroom Suite. Downtown and Stadium. Parking!

Corner House - Cozy Five Star 2 Bedroom Suite. Downtown and Stadium. Parking! is a holiday home in Round Bay, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, hot tub, kitchen, with kitchen, and parking.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,487.

From$355/night

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10 ★ 10 reviews

Downtown furnished apartment - walking distance to restaurants

Apartment, Round Bay

Downtown furnished apartment - walking distance to restaurants is a apartment in Round Bay, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Downtown furnished apartment - walking distance to restaurants

Downtown furnished apartment - walking distance to restaurants is a apartment in Round Bay, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,264.

From$323/night

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9.8 ★ 20 reviews

HUGE DISCOUNTS FOR STAYS BY THE WEEK AND MONTH! 1ST CLASS AMEMITIES!

Apartment, Round Bay

HUGE DISCOUNTS FOR STAYS BY THE WEEK AND MONTH! 1ST CLASS AMEMITIES! is a apartment in Round Bay, with parking and kitchen access. This stay gives travelers a comfortable base for exploring…

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About HUGE DISCOUNTS FOR STAYS BY THE WEEK AND MONTH! 1ST CLASS AMEMITIES!

HUGE DISCOUNTS FOR STAYS BY THE WEEK AND MONTH! 1ST CLASS AMEMITIES! is a apartment in Round Bay, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,776.

From$254/night

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9.2 ★ 17 reviews

Cute and Close to Downtown! Off street parking w/ short walk to Academy/Stadium

Holiday Home, Round Bay

Cute and Close to Downtown! Off street parking w/ short walk to Academy/Stadium is a holiday home in Round Bay, with parking and kitchen access. This stay gives travelers a comfortable base…

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About Cute and Close to Downtown! Off street parking w/ short walk to Academy/Stadium

Cute and Close to Downtown! Off street parking w/ short walk to Academy/Stadium is a holiday home in Round Bay, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,025.

From$289/night

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